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Highly enantio- and diastereoselective organocatalytic desymmetrization of prochiral cyclohexanones by simple direct aldol reaction catalyzed by proline

Highly enantio- and diastereoselective organocatalytic desymmetrization of prochiral cyclohexanones by simple direct aldol reaction catalyzed by proline
Highly enantio- and diastereoselective organocatalytic desymmetrization of prochiral cyclohexanones by simple direct aldol reaction catalyzed by proline
Panacea for aldol desymmetrizations: we describe an easy entry for the desymmetrization of 4-substituted-cyclohexanones catalyzed by proline, using as cocatalysts different hydrogen-bonding donors (see scheme), which dramatically improves the catalytic efficiency of proline in desymmetrization reactions.
aldol reaction, desymmetrization, hydrogen bonds, organocatalysis, proline
0947-6539
6564-6568
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Crovetto, Luis
45d4cd97-3fe5-4498-a861-bc06492eb09d
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Crovetto, Luis
45d4cd97-3fe5-4498-a861-bc06492eb09d
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Companyó, Xavier, Valero, Guillem, Crovetto, Luis, Moyano, Albert and Rios, Ramon (2009) Highly enantio- and diastereoselective organocatalytic desymmetrization of prochiral cyclohexanones by simple direct aldol reaction catalyzed by proline. Chemistry - A European Journal, 15 (27), 6564-6568. (doi:10.1002/chem.200900488). (PMID:19405053)

Record type: Article

Abstract

Panacea for aldol desymmetrizations: we describe an easy entry for the desymmetrization of 4-substituted-cyclohexanones catalyzed by proline, using as cocatalysts different hydrogen-bonding donors (see scheme), which dramatically improves the catalytic efficiency of proline in desymmetrization reactions.

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More information

e-pub ahead of print date: 29 April 2009
Published date: 6 July 2009
Keywords: aldol reaction, desymmetrization, hydrogen bonds, organocatalysis, proline
Organisations: Chemistry

Identifiers

Local EPrints ID: 340218
URI: http://eprints.soton.ac.uk/id/eprint/340218
ISSN: 0947-6539
PURE UUID: 7b22d609-8f83-4155-91c2-6ea5e082e471
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 15 Jun 2012 12:13
Last modified: 17 Dec 2019 01:38

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