期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 37, 页码 12121-12125出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807069
关键词
(4+3) cycloaddition; chiral phosphoric acids; cyclohepta[b]indoles; heterocycles; hydrogen bonds
资金
- ICSN
- CNRS
- Saclay University
A highly enantio- and diastereoselective formal (4+3) cycloaddition of 1,3-diene-1-carbamates with 3-indolylmethanols in the presence of a chiral phosphoric acid catalyst is reported. The approach described herein provides efficient access to 6-aminotetrahydrocyclohepta[b]indoles in good yields with mostly complete diastereoselectivity and excellent levels of enantioselectivity (> 98:2 dr and up to 98% ee). Mild reaction conditions, facile scale-up, and versatile derivatization highlight the practicality of this methodology. A mechanistic study suggests that cycloaddition occurs in a stepwise fashion, after the formation of an ion pair between the chiral catalytic phosphate and the intermediate carbocation.
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