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 react...

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Published inChemistry : a European journal Vol. 15; no. 27; pp. 6564 - 6568
Main Authors Companyó, Xavier, Valero, Guillem, Crovetto, Luis, Moyano, Albert, Rios, Ramon
Format Journal Article
LanguageEnglish
Published Weinheim WILEY‐VCH Verlag 06.07.2009
Wiley
Subjects
Aldehydes - chemistry
aldol reaction
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclization
Cyclohexanones - chemistry
desymmetrization
Hydrogen Bonding
hydrogen bonds
Molecular Structure
organocatalysis
Physical Sciences
proline
Proline - chemistry
Science & Technology
Stereoisomerism
organocatalysis
proline
aldol reaction
desymmetrization
THIOUREA
hydrogen bonds
DERIVATIVES
ENANTIOSELECTIVE DESYMMETRIZATION
MICHAEL ADDITION
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Summary: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. 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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200900488