Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones

David A. Evans; Jason S. Tedrow; Jared T. Shaw; C. Wade Downey

doi:10.1021/ja0119548

Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones

David A. Evans, Jason S. Tedrow, Jared T. Shaw, C. Wade Downey

Research output: Contribution to journal › Article › peer-review

291 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	392-393
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	124
Issue number	3
DOIs	https://doi.org/10.1021/ja0119548
State	Published - Jan 23 2002
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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10.1021/ja0119548

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abstract = "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.",

author = "Evans, {David A.} and Tedrow, {Jason S.} and Shaw, {Jared T.} and Downey, {C. Wade}",

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T1 - Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones

AU - Evans, David A.

AU - Tedrow, Jason S.

AU - Shaw, Jared T.

AU - Downey, C. Wade

PY - 2002/1/23

Y1 - 2002/1/23

N2 - 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.

AB - 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.

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Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones

Abstract

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