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Lewis Acid Catalyzed [3+2] Annulations of γ‐Butyrolactam‐Fused Donor–Acceptor Cyclopropanes with Aromatic Aldehydes and Aldimines
Author(s) -
Su Peiying,
Li Huimin,
Chen Wenlong,
Luo Gen,
Yang Gaosheng,
Chai Zhuo
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000818
Subject(s) - aldimine , chemistry , lewis acids and bases , catalysis , stereocenter , cyclopropane , organic chemistry , acceptor , stereochemistry , medicinal chemistry , enantioselective synthesis , ring (chemistry) , physics , condensed matter physics
A series of γ‐butyrolactam fused donor–acceptor (D–A) cyclopropanes were synthesized, and their reactivities in Lewis acid catalyzed [3+2] annulations with aromatic aldehydes and aldimines were studied. A range of γ‐butyrolactam fused tetrahydrofurans and γ‐butyrolactam fused pyrrolidines containing four contiguous stereogenic centers were generated in good‐to‐excellent yields and with exclusive diastereoselectivities and high enantiospecificity under the catalysis of 1 mol‐% of Al(OTf) 3 .