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Organocatalytic Enantioselective One‐Pot Synthesis and Application of Substituted 1,4‐Dihydropyridines—Hantzsch Ester Analogues
Author(s) -
Franke Patrick T.,
Johansen Rasmus L.,
Bertelsen Søren,
Jørgensen Karl Anker
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700360
Subject(s) - enantioselective synthesis , chemistry , organocatalysis , organic chemistry , combinatorial chemistry , catalysis
An easy and simple one‐pot approach for the formation of optically active substituted 1,4‐dihydropyridines by using asymmetric organocatalysis is presented. The one‐pot reaction of α,β‐unsaturated aldehydes with β‐diketones or β‐ketoesters and primary amines gives optically active 2,3‐substituted 1,4‐dihydropyridines in moderate yields and with enantioselectivities up to 95 % ee . It is also demonstrated that the optically active 1,4‐dihydropyridines can be used in situ for the direct enantioselective reduction of, for example, α‐ketoesters with high enantioselectivity.