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 journalArticle

276 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)392-393
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number3
DOIs
StatePublished - Jan 23 2002
Externally publishedYes

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Chromatography
Magnesium
Salts
Crystalline materials
Atmosphere
Water
3-hydroxybutanal
trimethylchlorosilane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones. / Evans, David A.; Tedrow, Jason S.; Shaw, Jared T.; Downey, C. Wade.

In: Journal of the American Chemical Society, Vol. 124, No. 3, 23.01.2002, p. 392-393.

Research output: Contribution to journalArticle

Evans, David A. ; Tedrow, Jason S. ; Shaw, Jared T. ; Downey, C. Wade. / Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones. In: Journal of the American Chemical Society. 2002 ; Vol. 124, No. 3. pp. 392-393.
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