Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones. |
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| Authors: | David A Evans Jason S Tedrow Jared T Shaw C Wade Downey |
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| Institution: | Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. |
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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. |
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