A New Henry/Michael/Retro‐Henry/Henry Domino Sequence Promoted by Bifunctional Organocatalysts | Zendy

Quintavalla Arianna | Zendy; Lombardo Marco | Zendy; Sanap Shrihari P. | Zendy; Trombini Claudio | Zendy

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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.

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