☆ 4.8 Article

Enantioselective Synthesis of Fused Polycyclic Tropanes via Dearomative [3+2] Cycloaddition Reactions of 2-Nitrobenzofurans

ORGANIC LETTERS (2020)

期刊

ORGANIC LETTERS

卷 22, 期 1, 页码 164-167

出版社

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.9b04108

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Chemistry, Organic

资金

National Natural Science Foundation of China [21672055, U1604283]
111 Project [D17007]
Program for Youth Backbone Teacher Training in University of Henan Province [2017GGJS042]

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摘要

A straight synthetic approach to fused polycyclic tropane scaffold formation through an asymmetric dearomatization cycloaddition process of 2-nitrobenzofurans with cyclic azomethine ylides was successfully developed. In the presence of a chiral copper complex, derived from Cu(OAc)(2) and a diphosphine ligand, a series of fused polycyclic tropane derivatives were obtained in high yields (75-91%) with excellent enantioselectivities (90-98%). The utility of this method was showcased by the facile transformation of product.

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