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 Communjournal_title
Nature communicationsauthors
Zhang Z,Bae HY,Guin J,Rabalakos C,van Gemmeren M,Leutzsch M,Klussmann M,List Bdoi
10.1038/ncomms12478subject
Has Abstractpub_date
2016-08-17 00:00:00pages
12478issn
2041-1723pii
ncomms12478journal_volume
7pub_type
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