Premium
Lewis Acid Catalyzed [3+2] Annulation of γ‐Butyrolactone Fused Cyclopropane with Aldehydes/Ketones
Author(s) -
Yang Pengfei,
Shen Yue,
Feng Manli,
Yang Gaosheng,
Chai Zhuo
Publication year - 2018
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.201800695
Subject(s) - annulation , chemistry , stereocenter , lewis acids and bases , cyclopropane , catalysis , reactivity (psychology) , bicyclic molecule , medicinal chemistry , stereochemistry , organic chemistry , enantioselective synthesis , ring (chemistry) , medicine , alternative medicine , pathology
The [3+2] annulation reaction of γ‐butyrolactone fused cyclopropanes with aldehydes or ketones under Lewis acid catalysis is described. Compared to their parent donor–acceptor (D–A) cyclopropanes, such fused bicyclic cyclopropanes demonstrated much better reactivity in this type of annulation process, providing accesses to densely substituted γ‐butyrolactone fused tetrahydrofurans bearing multiple adjacent stereogenic centers with a low catalyst loading (1–5 mol‐%), excellent diastereoselectivity, and a broad substrate scope under mild reaction conditions.