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- W1991844260 abstract "Additions of one to two equivalents of Lewis acids that include magnesium salts to free-radical reduction reactions involving ester functionalized radicals and (1R,2S,5R)-menthyldiphenyltin hydride 4, bis((1R,2S,5R)-menthyl)phenyltin hydride 5, tris((1R,2S,5R)-menthyl)tin hydride 6, bis((1R,2S,5R)-menthyl)-[8-(N,N-dimethylamino)naphthyl]tin hydride 12, bis((1R,2S,5R)-menthyl)-[1-((S)-N,N-dimethylaminoethyl)phenyl]tin hydride 13 or 3α-dimethylstannyl-5α-cholestane 14 result in remarkable enantioselectivities. Examples include (S)-naproxen ethyl ester 16, produced in 74% yield and greater than 99% ee at −78°C from the bromide and 5 in the presence of MgBr2, and ethyl (R)-N-trifluoroacetyl-d-phenylglycinate 18, obtained in 78% yield and 99% ee under identical conditions. Kinetic and computational studies provide insight into the origins of these observations." @default.
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- W1991844260 date "2003-10-01" @default.
- W1991844260 modified "2023-10-03" @default.
- W1991844260 title "Single enantiomer free-radical chemistry—Lewis acid-mediated reductions of racemic halides using chiral non-racemic stannanes" @default.
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- W1991844260 doi "https://doi.org/10.1016/j.tetasy.2003.07.012" @default.
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