Camphor Sulfonyl Hydrazines (CaSH) as Organocatalysts in Enantioselective Diels−Alder Reactions

Cyclic sulfonyl hydrazine was demonstrated for the first time as a new functionality for organocatalysis. A series of six-membered cyclic hydrazines derived from camphor sulfonic acid were synthesized. With trichloroacetic acid as cocatalyst, they are efficient organocatalysts for enantioselective D...

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Bibliographic Details
Published in:Organic letters 2008-06, Vol.10 (12), p.2421-2424
Main Authors: He, Hao, Pei, Bao-Jian, Chou, Ho-Hsuan, Tian, Tian, Chan, Wing-Hong, Lee, Albert W. M
Format: Article
Language:English
Subjects:
Camphor - analogs & derivatives
Camphor - chemistry
Catalysis
Cyclization
Heterocyclic Compounds, Bridged-Ring - chemistry
Hydrazines - chemical synthesis
Hydrazines - chemistry
Molecular Structure
Salts
Stereoisomerism
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Summary:Cyclic sulfonyl hydrazine was demonstrated for the first time as a new functionality for organocatalysis. A series of six-membered cyclic hydrazines derived from camphor sulfonic acid were synthesized. With trichloroacetic acid as cocatalyst, they are efficient organocatalysts for enantioselective Diels−Alder reactions with good chemical yields and up to 96% ee. The reactions took place in brine at 0 °C to room temperature.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8005826