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Organocatalytically Enantioselective Approach to Polysubstituted Tetrahydropyridines and Piperidines
Author(s) -
Yu Fang,
Zhang Xiaojing,
Jiang Yongwen
Publication year - 2011
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201180327
Subject(s) - chemistry , enantiopure drug , enantioselective synthesis , reductive amination , amination , organic chemistry , condensation , cascade , combinatorial chemistry , organocatalysis , catalysis , chromatography , physics , thermodynamics
A convenient and highly enantioselective method for assembly of functionalized 1,2,3,4,5‐pentasubstituted tetrahydropyridines and piperidines was developed. This method relies on preparing the required enantiopure cyclic semi‐acetals via an organocatalyzed Michael addition/cyclization cascade reaction of aldehydes and α ‐keto‐ α , β ‐unsaturated esters, and subsequent reductive amination/condensation with primary amines.