期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 43, 页码 18964-18969出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202007068
关键词
bicyclic acetal; copper catalyst; cyclopropanation; enantioselective; spiroaminal
资金
- NSFC [21772224, 91956103]
- CAS [QYZDY-SSW-SLH016, XDB20000000]
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 beta-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.
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