1997 stereochemistry

stereochemistry (general, optical resolution)O 0030

06 - 0291,4-Asymmetric Induction in the Chromium(II)- and Indium-Mediated Coupling of Allyl Bromides to Aldehydes. — Treatmentof allyl bromides of type (I), which are generated from methyl acrylate, withaldehydes under Cr2+-mediated conditions is found to give syn-4-alkoxyalkanolslike (III) in good yield and diastereoselectivity. The nature of the substituentR1 slightly affects the stereoselectivity while the nature of the etheral protectinggroup has no effect on the selectivity. The indium-mediated coupling leadsto similar results. — (MAGUIRE, R. J.; MULZER, J.; BATS, J. W.; J.Org. Chem. 61 (1996) 20, 6936-6940; Inst. Org. Chem., J. W. Goethe-Univ.,D-60439 Frankfurt/M., Germany; EN)

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