Premium
A Versatile Enantioselective Catalytic Cyclopropanation‐Rearrangement Approach to the Divergent Construction of Chiral Spiroaminals and Fused Bicyclic Acetals
Author(s) -
Zhou Li,
Yan WenGuang,
Sun XiuLi,
Wang Lijia,
Tang Yong
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007068
Subject(s) - enantioselective synthesis , stereocenter , cyclopropanation , bicyclic molecule , chemistry , combinatorial chemistry , stereochemistry , substrate (aquarium) , catalysis , organic chemistry , oceanography , geology
A highly enantioselective synthesis of various chiral heterobicyclic molecules including spiroaminals and fused bicyclic acetals has been developed via a chiral copper catalyzed cyclopropanation‐rearrangement (CP‐RA) approach under mild reaction conditions. Remarkably, the asymmetric CP‐RA for exocyclic vinyl substrates without a pro‐stereogenic carbon at the β‐position has been realized for the first time and a broad substrate scope with excellent results (33 examples; 34–99 % yields; >95/5 dr and 91–99 % ee ) has been achieved. An application of a successive enantioselective CP‐RA approach was also described, providing a concise access to complex chiral heteropolycycles.