Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes.

Abstract:

:Due to the high versatility of chiral cyanohydrins, the catalytic asymmetric cyanation reaction of carbonyl compounds has attracted widespread interest. However, efficient protocols that function at a preparative scale with low catalyst loading are still rare. Here, asymmetric counteranion-directed Lewis acid organocatalysis proves to be remarkably successful in addressing this problem and enabled a molar-scale cyanosilylation in quantitative yield and with excellent enantioselectivity. Also, the catalyst loading could be lowered to a part-per-million level (50 ppm: 0.005 mol%). A readily accessible chiral disulfonimide was used, which in combination with trimethylsilyl cyanide, turned into the active silylium Lewis acid organocatalyst. The nature of a peculiar phenomenon referred to as a "dormant period", which is mainly induced by water, was systematically investigated by means of in situ Fourier transform infrared analysis.

journal_name

Nat Commun

journal_title

Nature communications

authors

Zhang Z,Bae HY,Guin J,Rabalakos C,van Gemmeren M,Leutzsch M,Klussmann M,List B

doi

10.1038/ncomms12478

subject

Has Abstract

pub_date

2016-08-17 00:00:00

pages

12478

issn

2041-1723

pii

ncomms12478

journal_volume

7

pub_type

杂志文章
  • Non defect-stabilized thermally stable single-atom catalyst.

    abstract::Surface-supported isolated atoms in single-atom catalysts (SACs) are usually stabilized by diverse defects. The fabrication of high-metal-loading and thermally stable SACs remains a formidable challenge due to the difficulty of creating high densities of underpinning stable defects. Here we report that isolated Pt ato...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-018-08136-3

    authors: Lang R,Xi W,Liu JC,Cui YT,Li T,Lee AF,Chen F,Chen Y,Li L,Li L,Lin J,Miao S,Liu X,Wang AQ,Wang X,Luo J,Qiao B,Li J,Zhang T

    更新日期:2019-01-16 00:00:00

  • High conductance values in π-folded molecular junctions.

    abstract::Folding processes play a crucial role in the development of function in biomacromolecules. Recreating this feature on synthetic systems would not only allow understanding and reproducing biological functions but also developing new functions. This has inspired the development of conformationally ordered synthetic olig...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms15195

    authors: Carini M,Ruiz MP,Usabiaga I,Fernández JA,Cocinero EJ,Melle-Franco M,Diez-Perez I,Mateo-Alonso A

    更新日期:2017-05-18 00:00:00

  • Taxonomic and functional diversity change is scale dependent.

    abstract::Estimates of recent biodiversity change remain inconsistent, debated, and infrequently assessed for their functional implications. Here, we report that spatial scale and type of biodiversity measurement influence evidence of temporal biodiversity change. We show a pervasive scale dependence of temporal trends in taxon...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-018-04889-z

    authors: Jarzyna MA,Jetz W

    更新日期:2018-07-02 00:00:00

  • PARP9 and PARP14 cross-regulate macrophage activation via STAT1 ADP-ribosylation.

    abstract::Despite the global impact of macrophage activation in vascular disease, the underlying mechanisms remain obscure. Here we show, with global proteomic analysis of macrophage cell lines treated with either IFNγ or IL-4, that PARP9 and PARP14 regulate macrophage activation. In primary macrophages, PARP9 and PARP14 have o...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms12849

    authors: Iwata H,Goettsch C,Sharma A,Ricchiuto P,Goh WW,Halu A,Yamada I,Yoshida H,Hara T,Wei M,Inoue N,Fukuda D,Mojcher A,Mattson PC,Barabási AL,Boothby M,Aikawa E,Singh SA,Aikawa M

    更新日期:2016-10-31 00:00:00

  • Electron-vibration coupling induced renormalization in the photoemission spectrum of diamondoids.

    abstract::The development of theories and methods devoted to the accurate calculation of the electronic quasi-particle states and levels of molecules, clusters and solids is of prime importance to interpret the experimental data. These quantum systems are often modelled by using the Born-Oppenheimer approximation where the coup...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms11327

    authors: Gali A,Demján T,Vörös M,Thiering G,Cannuccia E,Marini A

    更新日期:2016-04-22 00:00:00

  • Ray-optics cloaking devices for large objects in incoherent natural light.

    abstract::A cloak that can hide living creatures from sight is a common feature of mythology but still remains unrealized as a practical device. To preserve the wave phase, the previous cloaking solution proposed by Pendry and colleagues required transformation of the electromagnetic space around the hidden object in such a way...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms3652

    authors: Chen H,Zheng B,Shen L,Wang H,Zhang X,Zheludev NI,Zhang B

    更新日期:2013-01-01 00:00:00

  • Organocatalytic enantio- and diastereoselective cycloetherification via dynamic kinetic resolution of chiral cyanohydrins.

    abstract::Enantioselective approaches to synthesize six-membered oxacycles with multiple stereogenic centres are in high demand to enable the discovery of new therapeutic agents. Here we present a concise organocatalytic cycloetherification for the highly enantio- and diastereoselective synthesis of tetrahydropyrans involving s...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-017-01099-x

    authors: Yoneda N,Fujii Y,Matsumoto A,Asano K,Matsubara S

    更新日期:2017-11-09 00:00:00

  • Biased localization of actin binding proteins by actin filament conformation.

    abstract::The assembly of actin filaments into distinct cytoskeletal structures plays a critical role in cell physiology, but how proteins localize differentially to these structures within a shared cytoplasm remains unclear. Here, we show that the actin-binding domains of accessory proteins can be sensitive to filament conform...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-020-19768-9

    authors: Harris AR,Jreij P,Belardi B,Joffe AM,Bausch AR,Fletcher DA

    更新日期:2020-11-25 00:00:00

  • Specifically modified Env immunogens activate B-cell precursors of broadly neutralizing HIV-1 antibodies in transgenic mice.

    abstract::VRC01-class broadly neutralizing HIV-1 antibodies protect animals from experimental infection and could contribute to an effective vaccine response. Their predicted germline forms (gl) bind Env inefficiently, which may explain why they are not elicited by HIV-1 Env-immunization. Here we show that an optimized Env immu...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms10618

    authors: McGuire AT,Gray MD,Dosenovic P,Gitlin AD,Freund NT,Petersen J,Correnti C,Johnsen W,Kegel R,Stuart AB,Glenn J,Seaman MS,Schief WR,Strong RK,Nussenzweig MC,Stamatatos L

    更新日期:2016-02-24 00:00:00

  • Structure and substrate selectivity of the 750-kDa α6β6 holoenzyme of geranyl-CoA carboxylase.

    abstract::Geranyl-CoA carboxylase (GCC) is essential for the growth of Pseudomonas organisms with geranic acid as the sole carbon source. GCC has the same domain organization and shares strong sequence conservation with the related biotin-dependent carboxylases 3-methylcrotonyl-CoA carboxylase (MCC) and propionyl-CoA carboxylas...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms9986

    authors: Jurado AR,Huang CS,Zhang X,Zhou ZH,Tong L

    更新日期:2015-11-23 00:00:00

  • YAP/TAZ direct commitment and maturation of lymph node fibroblastic reticular cells.

    abstract::Fibroblastic reticular cells (FRCs) are immunologically specialized myofibroblasts of lymphoid organ, and FRC maturation is essential for structural and functional properties of lymph nodes (LNs). Here we show that YAP and TAZ (YAP/TAZ), the final effectors of Hippo signaling, regulate FRC commitment and maturation. S...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-020-14293-1

    authors: Choi SY,Bae H,Jeong SH,Park I,Cho H,Hong SP,Lee DH,Lee CK,Park JS,Suh SH,Choi J,Yang MJ,Jang JY,Onder L,Moon JH,Jeong HS,Adams RH,Kim JM,Ludewig B,Song JH,Lim DS,Koh GY

    更新日期:2020-01-24 00:00:00

  • Genome-wide CRISPR screen identifies ELP5 as a determinant of gemcitabine sensitivity in gallbladder cancer.

    abstract::Gemcitabine is the first-line treatment for locally advanced and metastatic gallbladder cancer (GBC), but poor gemcitabine response is universal. Here, we utilize a genome-wide CRISPR screen to identify that loss of ELP5 reduces the gemcitabine-induced apoptosis in GBC cells in a P53-dependent manner through the Elong...

    journal_title:Nature communications

    pub_type: 临床试验,杂志文章

    doi:10.1038/s41467-019-13420-x

    authors: Xu S,Zhan M,Jiang C,He M,Yang L,Shen H,Huang S,Huang X,Lin R,Shi Y,Liu Q,Chen W,Mohan M,Wang J

    更新日期:2019-12-02 00:00:00

  • Laminin regulates PDGFRβ(+) cell stemness and muscle development.

    abstract::Muscle-resident PDGFRβ(+) cells, which include pericytes and PW1(+) interstitial cells (PICs), play a dual role in muscular dystrophy. They can either undergo myogenesis to promote muscle regeneration or differentiate into adipocytes and other cells to compromise regeneration. How the differentiation and fate determin...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms11415

    authors: Yao Y,Norris EH,Mason CE,Strickland S

    更新日期:2016-05-03 00:00:00

  • Hydrodynamic phonon transport in suspended graphene.

    abstract::Recent studies of thermal transport in nanomaterials have demonstrated the breakdown of Fourier's law through observations of ballistic transport. Despite its unique features, another instance of the breakdown of Fourier's law, hydrodynamic phonon transport, has drawn less attention because it has been observed only a...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms7290

    authors: Lee S,Broido D,Esfarjani K,Chen G

    更新日期:2015-02-18 00:00:00

  • Beam electrons as a source of Hα flare ribbons.

    abstract::The observations of solar flare onsets show rapid increase of hard and soft X-rays, ultra-violet emission with large Doppler blue shifts associated with plasma upflows, and Hα hydrogen emission with red shifts up to 1-4 Å. Modern radiative hydrodynamic models account well for blue-shifted emission, but struggle to rep...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms15905

    authors: Druett M,Scullion E,Zharkova V,Matthews S,Zharkov S,Rouppe Van der Voort L

    更新日期:2017-06-27 00:00:00

  • Author Correction: Ultrafast bridge planarization in donor-π-acceptor copolymers drives intramolecular charge transfer.

    abstract::The original version of this Article omitted the following from the Acknowledgements:"Satish Patil thanks Department of Science and Technology, New Delhi, India for a Swarnajayanti fellowship."This has now been corrected in both the PDF and HTML versions of the Article. ...

    journal_title:Nature communications

    pub_type: 杂志文章,已发布勘误

    doi:10.1038/s41467-017-02574-1

    authors: Roy P,Jha A,Yasarapudi VB,Ram T,Puttaraju B,Patil S,Dasgupta J

    更新日期:2018-01-03 00:00:00

  • Ancient genomes reveal social and genetic structure of Late Neolithic Switzerland.

    abstract::Genetic studies of Neolithic and Bronze Age skeletons from Europe have provided evidence for strong population genetic changes at the beginning and the end of the Neolithic period. To further understand the implications of these in Southern Central Europe, we analyze 96 ancient genomes from Switzerland, Southern Germa...

    journal_title:Nature communications

    pub_type: 历史文章,杂志文章

    doi:10.1038/s41467-020-15560-x

    authors: Furtwängler A,Rohrlach AB,Lamnidis TC,Papac L,Neumann GU,Siebke I,Reiter E,Steuri N,Hald J,Denaire A,Schnitzler B,Wahl J,Ramstein M,Schuenemann VJ,Stockhammer PW,Hafner A,Lösch S,Haak W,Schiffels S,Krause J

    更新日期:2020-04-20 00:00:00

  • Implementing a universal gate set on a logical qubit encoded in an oscillator.

    abstract::A logical qubit is a two-dimensional subspace of a higher dimensional system, chosen such that it is possible to detect and correct the occurrence of certain errors. Manipulation of the encoded information generally requires arbitrary and precise control over the entire system. Whether based on multiple physical qubit...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-017-00045-1

    authors: Heeres RW,Reinhold P,Ofek N,Frunzio L,Jiang L,Devoret MH,Schoelkopf RJ

    更新日期:2017-07-21 00:00:00

  • P38α/JNK signaling restrains erythropoiesis by suppressing Ezh2-mediated epigenetic silencing of Bim.

    abstract::While erythropoietin (EPO) constitutes the major treatment for anemia, a range of anemic disorders remain resistant to EPO treatment. The need for alternative therapeutic strategies requires the identification of mechanisms that physiologically restrain erythropoiesis. Here we show that P38α restrains erythropoiesis i...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-018-05955-2

    authors: Hu P,Nebreda AR,Hanenberg H,Kinnebrew GH,Ivan M,Yoder MC,Filippi MD,Broxmeyer HE,Kapur R

    更新日期:2018-08-29 00:00:00

  • Elucidation of the biosynthesis of carnosic acid and its reconstitution in yeast.

    abstract::Rosemary extracts containing the phenolic diterpenes carnosic acid and its derivative carnosol are approved food additives used in an increasingly wide range of products to enhance shelf-life, thanks to their high anti-oxidant activity. We describe here the elucidation of the complete biosynthetic pathway of carnosic ...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms12942

    authors: Scheler U,Brandt W,Porzel A,Rothe K,Manzano D,Božić D,Papaefthimiou D,Balcke GU,Henning A,Lohse S,Marillonnet S,Kanellis AK,Ferrer A,Tissier A

    更新日期:2016-10-05 00:00:00

  • Electric eels use high-voltage to track fast-moving prey.

    abstract::Electric eels (Electrophorus electricus) are legendary for their ability to incapacitate fish, humans, and horses with hundreds of volts of electricity. The function of this output as a weapon has been obvious for centuries but its potential role for electroreception has been overlooked. Here it is shown that electric...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms9638

    authors: Catania KC

    更新日期:2015-10-20 00:00:00

  • A cocktail of three virulent bacteriophages prevents Vibrio cholerae infection in animal models.

    abstract::Effective prevention strategies will be essential in reducing disease burden due to bacterial infections. Here we harness the specificity and rapid-acting properties of bacteriophages as a potential prophylaxis therapy for cholera, a severely dehydrating disease caused by Vibrio cholerae. To this end, we test a cockta...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms14187

    authors: Yen M,Cairns LS,Camilli A

    更新日期:2017-02-01 00:00:00

  • Multiple truncated isoforms of MAVS prevent its spontaneous aggregation in antiviral innate immune signalling.

    abstract::In response to virus infection, RIG-I-like receptors (RLRs) sense virus RNA and induce MAVS to form prion-like aggregates to further propagate antiviral signalling. Although monomeric MAVS recombinant protein can assemble into prion-like filaments spontaneously in vitro, endogenous MAVS in cells is prevented from aggr...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms15676

    authors: Qi N,Shi Y,Zhang R,Zhu W,Yuan B,Li X,Wang C,Zhang X,Hou F

    更新日期:2017-06-13 00:00:00

  • Automated acquisition of explainable knowledge from unannotated histopathology images.

    abstract::Deep learning algorithms have been successfully used in medical image classification. In the next stage, the technology of acquiring explainable knowledge from medical images is highly desired. Here we show that deep learning algorithm enables automated acquisition of explainable features from diagnostic annotation-fr...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-019-13647-8

    authors: Yamamoto Y,Tsuzuki T,Akatsuka J,Ueki M,Morikawa H,Numata Y,Takahara T,Tsuyuki T,Tsutsumi K,Nakazawa R,Shimizu A,Maeda I,Tsuchiya S,Kanno H,Kondo Y,Fukumoto M,Tamiya G,Ueda N,Kimura G

    更新日期:2019-12-18 00:00:00

  • Experimental noise cutoff boosts inferability of transcriptional networks in large-scale gene-deletion studies.

    abstract::Generating a comprehensive map of molecular interactions in living cells is difficult and great efforts are undertaken to infer molecular interactions from large-scale perturbation experiments. Here, we develop the analytical and numerical tools to quantify the fundamental limits for inferring transcriptional networks...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-017-02489-x

    authors: Blum CF,Heramvand N,Khonsari AS,Kollmann M

    更新日期:2018-01-09 00:00:00

  • Gas-responsive porous magnet distinguishes the electron spin of molecular oxygen.

    abstract::Gas-sensing materials are becoming increasingly important in our society, requiring high sensitivity to differentiate similar gases like N2 and O2. For the design of such materials, the driving force of electronic host-guest interaction or host-framework changes during the sorption process has commonly been considered...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-018-07889-1

    authors: Kosaka W,Liu Z,Zhang J,Sato Y,Hori A,Matsuda R,Kitagawa S,Miyasaka H

    更新日期:2018-12-21 00:00:00

  • Chaperone-mediated ordered assembly of the SAGA and NuA4 transcription co-activator complexes in yeast.

    abstract::Transcription initiation involves the coordinated activities of large multimeric complexes, but little is known about their biogenesis. Here we report several principles underlying the assembly and topological organization of the highly conserved SAGA and NuA4 co-activator complexes, which share the Tra1 subunit. We s...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-019-13243-w

    authors: Elías-Villalobos A,Toullec D,Faux C,Séveno M,Helmlinger D

    更新日期:2019-11-20 00:00:00

  • Non-additivity of molecule-surface van der Waals potentials from force measurements.

    abstract::Van der Waals (vdW) forces act ubiquitously in condensed matter. Despite being weak on an atomic level, they substantially influence molecular and biological systems due to their long range and system-size scaling. The difficulty to isolate and measure vdW forces on a single-molecule level causes our present understan...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms6568

    authors: Wagner C,Fournier N,Ruiz VG,Li C,Müllen K,Rohlfing M,Tkatchenko A,Temirov R,Tautz FS

    更新日期:2014-11-26 00:00:00

  • Integrated digital inverters based on two-dimensional anisotropic ReS2 field-effect transistors.

    abstract::Semiconducting two-dimensional transition metal dichalcogenides are emerging as top candidates for post-silicon electronics. While most of them exhibit isotropic behaviour, lowering the lattice symmetry could induce anisotropic properties, which are both scientifically interesting and potentially useful. Here we prese...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/ncomms7991

    authors: Liu E,Fu Y,Wang Y,Feng Y,Liu H,Wan X,Zhou W,Wang B,Shao L,Ho CH,Huang YS,Cao Z,Wang L,Li A,Zeng J,Song F,Wang X,Shi Y,Yuan H,Hwang HY,Cui Y,Miao F,Xing D

    更新日期:2015-05-07 00:00:00

  • Disposable ultrasound-sensing chronic cranial window by soft nanoimprinting lithography.

    abstract::Chronic cranial window (CCW) is an essential tool in enabling longitudinal imaging and manipulation of various brain activities in live animals. However, an active CCW capable of sensing the concealed in vivo environment while simultaneously providing longitudinal optical access to the brain is not currently available...

    journal_title:Nature communications

    pub_type: 杂志文章

    doi:10.1038/s41467-019-12178-6

    authors: Li H,Dong B,Zhang X,Shu X,Chen X,Hai R,Czaplewski DA,Zhang HF,Sun C

    更新日期:2019-09-19 00:00:00