Direct Asymmetric Aldol Reaction with Recyclable Fluorous Organocatalyst

Direct asymmetric aldol reactions of aldehydes with ketones in the presence of a catalytic amount of fluorous sulfonamide 4 and trifluoroacetic acid result in the corresponding aldol products in high yields with up to 96% ee. The fluorous organocatalyst 4 can be readily recovered from the reaction m...

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Bibliographic Details
Published in:Organic letters 2010-04, Vol.12 (7), p.1620-1623
Main Authors: Miura, Tsuyoshi, Imai, Kie, Ina, Mariko, Tada, Norihiro, Imai, Nobuyuki, Itoh, Akichika
Format: Article
Language:English
Subjects:
Alcohols - chemical synthesis
Alcohols - chemistry
Aldehydes - chemistry
Catalysis
Cyclization
Hydrocarbons, Fluorinated - chemistry
Ketones - chemistry
Molecular Structure
Solid Phase Extraction
Stereoisomerism
Sulfonamides - chemistry
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Summary:Direct asymmetric aldol reactions of aldehydes with ketones in the presence of a catalytic amount of fluorous sulfonamide 4 and trifluoroacetic acid result in the corresponding aldol products in high yields with up to 96% ee. The fluorous organocatalyst 4 can be readily recovered from the reaction mixture by fluorous solid-phase extraction and could be reused without a significant loss of the catalytic activity and enantioselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1003719