Enantiomeric Catalytic Formal Thiolation of 2,5‐Dimethyl‐3‐[1‐(arylsulfonyl)alkyl]pyrroles in an Oil/Water Biphasic System | Zendy

Chen Ping | Zendy; Yang Qin | Zendy; Lu Shengmei | Zendy; Wang Peng | Zendy; Liu Yan | Zendy; Li Can | Zendy

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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.

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