Magnesium halide-catalyzed anti-aldol reactions of chiral N-acylthiazolidinethiones |
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| Authors: | Evans David A Downey C Wade Shaw Jared T Tedrow Jason S |
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| Affiliation: | Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu |
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| Abstract: | [reaction: see text] Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the illustrated anti diastereomer. This reaction is catalyzed by 10% MgBr2.OEt2 in the presence of triethylamine and chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes. |
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