Abstract：
:Rearrangement reactions have attracted considerable interest over the past decades due to their high bond-forming efficiency and atom economy in the construction of complex organic architectures. In contrast to the well-established [3,3]-rearrangement, [1,3] O-to-C rearrangement has been far less vigorously investigated, and stereospecific [1,3]-rearrangement is extremely rare. Here, we report a metal-free intramolecular hydroalkoxylation/[1,3]-rearrangement, leading to the practical and atom-economical assembly of various valuable medium-sized lactams with wide substrate scope and excellent diastereoselectivity. Moreover, such an asymmetric cascade cyclization has also been realized by chiral Brønsted acid-catalyzed kinetic resolution. In addition, biological tests reveal that some of these medium-sized lactams displayed their bioactivity as antitumor agents against melanoma cells, esophageal cancer cells and breast cancer cells. A mechanistic rationale for the reaction is further supported by control experiments and theoretical calculations.
journal_name
Nat Communjournal_title
Nature communicationsauthors
Zhou B,Zhang YQ,Zhang K,Yang MY,Chen YB,Li Y,Peng Q,Zhu SF,Zhou QL,Ye LWdoi
10.1038/s41467-019-11245-2subject
Has Abstractpub_date
2019-07-19 00:00:00pages
3234issue
1issn
2041-1723pii
10.1038/s41467-019-11245-2journal_volume
10pub_type
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