Diastereoselective Magnesium Halide-Catalyzed anti-Aldol Reactions of Chiral N-Acyloxazolidinones

A chiral auxilliary-based direct aldol reaction is reported. The reactions are catalytic in magnesium salts and are facilitated by silylation with chlorotrimethylsilane. The adducts isolated are in high diastereoselectivity (up to 32:1 dr) and favor the anti-aldol diastereomer B. Reactions are opera...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-01, Vol.124 (3), p.392-393
Main Authors: Evans, David A, Tedrow, Jason S, Shaw, Jared T, Downey, C. Wade
Format: Article
Language:English
Subjects:
Benzaldehydes - chemistry
Catalysis
Chemical reactivity
Chemistry
Exact sciences and technology
Magnesium Chloride - chemistry
Organic chemistry
Oxazolidinones - chemistry
Reactivity and mechanisms
Stereoisomerism
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Summary:A chiral auxilliary-based direct aldol reaction is reported. The reactions are catalytic in magnesium salts and are facilitated by silylation with chlorotrimethylsilane. The adducts isolated are in high diastereoselectivity (up to 32:1 dr) and favor the anti-aldol diastereomer B. Reactions are operationally simple and can be run under ambient atmosphere without rigorous exclusion of water. Many of the adducts are highly crystalline and a single diastereomer can be isolated without chromatography.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0119548