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Enantioselective metal-free reduction of ketones by a user-friendly silane with a reusable chiral additive

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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… Click to show full abstract

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.

Keywords: free reduction; enantioselective metal; reduction ketones; user friendly; metal free; ketones user

Journal Title: Tetrahedron Letters
Year Published: 2018

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