Opening of Tartrate Acetals Using Dialkylboron Bromide: Evidence for Stereoselectivity Downstream from Ring Fission
Journal of the American Chemical Society2002Vol. 125(2), pp. 428–436
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Yvan Guindon, William W. Ogilvie, Josée Bordeleau, Wei Li Cui, Kathleen A. Durkin, Vida Gorys, Hélène Jûteau, René Lemieux, Dennis C. Liotta, Bruno Simoneau, Christiane Yoakim
Abstract
Johnson-type acetals derived from dimethyl tartrate give, after opening with Me(2)BBr and cuprate displacement, secondary alcohols with high diastereoselectivity (>30:1). The mechanism proposed for the induction of diastereoselectivity is downstream from the ring fission. It implies a direct participation of the Lewis acid as a source of nucleophile and the stereospecific transformation of the resulting bromo acetal through an invertive and temperature-dependent process. The acetals are prepared by reaction of the desired aldehyde with dimethyl tartrate. Removal of the auxiliary is accomplished through SmI(2) reduction or by an addition-elimination protocol using methoxide.
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