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A Practical and Enantioselective Approach to Tetrahydrocarbazoles by Asymmetric Organocatalysis
Author(s) -
Zhu XiaoYu,
An XiaoLei,
Li ChangFeng,
Zhang FuGen,
Hua QiuLin,
Chen JiaRong,
Xiao WenJing
Publication year - 2011
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201000379
Subject(s) - enantioselective synthesis , organocatalysis , pyrrole , intramolecular force , chemistry , computer science , alkylation , combinatorial chemistry , organic chemistry , catalysis
A highly enantioselective intramolecular Friedel–Crafts‐type alkylation of ω‐indolyl α,β‐unsaturated aldehydes has been disclosed. This reaction allows efficient access to functionalized tetrahydrocarbazoles in high yields (up to 95 %) with excellent enantioselectivities (up to 98 % ee ). This procedure is also successful in the asymmetric synthesis of pyrrole‐fused heterocycles (up to 88 % ee ).
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