Chiral Diols:  A New Class of Additives for Direct Aldol Reaction Catalyzed by l-Proline

Nine C 2 symmetric diols have been examined as additives in the l-proline-catalyzed direct aldol reaction with significant improvement in enantioselectivity, conversion efficiency, and yield. Loading of 1 mol % of (S)-BINOL leads to the desired products in up to 98% ee and 90% yield. A transition st...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 71; no. 25; pp. 9510 - 9512
Main Authors Zhou, Yan, Shan, Zixing
Format Journal Article
LanguageEnglish
Published Washington, DC American Chemical Society 08.12.2006
Subjects
Alcohols - chemistry
Catalysis
Chemistry
Exact sciences and technology
Organic chemistry
Proline - chemistry
Stereoisomerism
α-Aminoacid
Diol
Catalytic reaction
Enantioselectivity
Nitrogen heterocycle
Aminoacid
Transition state
Phenols
Proline
Enantiomeric excess
Chiral compound
Aldol condensation
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Summary:Nine C 2 symmetric diols have been examined as additives in the l-proline-catalyzed direct aldol reaction with significant improvement in enantioselectivity, conversion efficiency, and yield. Loading of 1 mol % of (S)-BINOL leads to the desired products in up to 98% ee and 90% yield. A transition state is proposed.
Bibliography:ark:/67375/TPS-D769FRFR-W
istex:B4D137F8EE04453A5AA29F29EFFF254926AC4360
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060802y