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Organocatalytic Heterocyclization Driven by Dynamic Kinetic Resolution: Enantioselective Access to Multi‐heteroatomic Cyclic Structures Mediated by Cinchona Alkaloid‐based Catalysts
Author(s) -
Capaccio V.,
Capobianco A.,
Stanzione A.,
Pierri G.,
Tedesco C.,
Di Mola A.,
Massa A.,
Palombi L.
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700472
Subject(s) - chemistry , cinchona , enantioselective synthesis , kinetic resolution , desymmetrization , cinchona alkaloids , catalysis , organocatalysis , organic chemistry , combinatorial chemistry , cinchonidine , stereochemistry
A new class of multi‐heteroatomic cyclic compounds containing N, S and O has been achieved in an enantioselective fashion via desymmetrization of 2‐cyano‐N‐tosylbenzylidenimine with thiols and subsequent catalytic dynamic kinetic resolution (DKR). Both organo‐ and phase transfer catalysis based on cinchona alkaloids having two H‐bonding coordination sites proved to be effective to furnish very good level of enantioselectivity (up to 95:5 er ) in the heterocyclization of racemic N‐Tosyl‐protected N,S‐acetals deriving from 2‐formyl benzonitriles.