495404-68-7Relevant academic research and scientific papers
Opening of tartrate acetals using dialkylboron bromide: Evidence for stereoselectivity downstream from ring fission
Guindon, Yvan,Ogilvie, William W.,Bordeleau, Josee,Cui, Wei Li,Durkin, Kathy,Gorys, Vida,Juteau, Helene,Lemieux, Rene,Liotta, Dennis,Simoneau, Bruno,Yoakim, Christiane
, p. 428 - 436 (2003)
Johnson-type acetals derived from dimethyl tartrate give, after opening with Me2BBr 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 Sml2 reduction or by an addition - elimination protocol using methoxide.
