Enantioselective metal-free reduction of ketones by a user-friendly silane with a reusable chiral additive |
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| Authors: | Sami E. Varjosaari Vladislav Skrypai Sharon M. Herlugson Thomas M. Gilbert Marc J. Adler |
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| Affiliation: | 1. Department of Chemistry & Biochemistry, Northern Illinois University, 1425 W. Lincoln Hwy, Dekalb, IL 60115, USA;2. Department of Chemistry & Biology, Ryerson University, 350 Victoria Street, Toronto, ON M5B 2K3, Canada |
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| Abstract: | ![]()
1-Hydrosilatrane, a safe and easy-to-handle reducing reagent that can be inexpensively accessed, has been shown to reduce prochiral ketones asymmetrically in the presence of chiral 1,2-aminoalcohols with ees ranging from 8% to 86%. The best result was achieved using ephedrine as the source of chirality, which is readily commercially available. The additive can be recovered through extraction and reused without any erosion of enantioselectivity. |
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| Keywords: | Hydrosilylation Asymmetric ketone reduction Synthesis of chiral alcohols |
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