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.

Organocatalytic Heterocyclization Driven by Dynamic Kinetic Resolution: Enantioselective Access to Multi-heteroatomic Cyclic Structures Mediated by Cinchona Alkaloid-based Catalysts

CAPACCIO, VITO;CAPOBIANCO, AMEDEO;Pierri, G.;TEDESCO, Consiglia;DI MOLA, ANTONIA;MASSA, Antonio;PALOMBI, Laura
2017

Abstract

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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/4688953
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