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A New Henry/Michael/Retro‐Henry/Henry Domino Sequence Promoted by Bifunctional Organocatalysts
Author(s) -
Quintavalla Arianna,
Lombardo Marco,
Sanap Shrihari P.,
Trombini Claudio
Publication year - 2013
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.201201135
Subject(s) - stereocenter , bifunctional , chemistry , domino , cinchona , nitroaldol reaction , organocatalysis , stereoselectivity , michael reaction , cyclohexanes , sequence (biology) , enantioselective synthesis , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , biochemistry
A highly stereoselective route to densely functionalized cyclohexanes is described, via a Cinchona ‐based bifunctional organocatalyzed Henry/Michael/retro‐Henry/Henry domino reaction. The peculiar stereoconvergent mechanism allows the creation of up to four contiguous stereocenters in a highly stereodefined manner starting from both achiral aldehydes and racemic nitro alcohols. The simple and efficient protocol can be exploited to synthesize a wide range of substrates and also useful bioactive molecules.