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Enantiomeric Catalytic Formal Thiolation of 2,5‐Dimethyl‐3‐[1‐(arylsulfonyl)alkyl]pyrroles in an Oil/Water Biphasic System
Author(s) -
Chen Ping,
Yang Qin,
Lu Shengmei,
Wang Peng,
Liu Yan,
Li Can
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601180
Subject(s) - chemistry , enantioselective synthesis , alkyl , cinchona , enantiomer , bifunctional , imine , pyrrole , organocatalysis , organic chemistry , catalysis
The asymmetric synthesis of 3‐ sec ‐substituted pyrrole derivatives through vinylogous imine intermediates generated in situ from 2,5‐dimethyl‐3‐[1‐(arylsulfonyl)alkyl]pyrroles with high activity and enantioselectivity (up to 98 % ee ) was examined. Employing a cinchona alkaloid based chiral bifunctional organocatalyst, the reaction of tritylthiol to sulfonylpyrroles delivered a series of highly enantioselective sulfur‐containing 3‐ sec ‐substituted pyrroles.