Opening of tartrate acetals using dialkylboron bromide: evidence for stereoselectivity downstream from ring fission |
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Authors: | Guindon Yvan Ogilvie William W Bordeleau Josée Cui Wei Li Durkin Kathy Gorys Vida Juteau Hélène Lemieux René Liotta Dennis Simoneau Bruno Yoakim Christiane |
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Affiliation: | Boehringer Ingelheim (Canada) Ltd., Bio-Méga Research Division, 2100 rue Cunard, Laval Québec, Canada H7S 2G5. |
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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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