Control of diastereoselectivity by solvent effects in the addition of Grignard reagents to enantiopure t-butylsulfinimine: syntheses of the stereoisomers of the hydroxyl derivatives of sibutramine |
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Authors: | Lu Bruce Z Senanayake Chris Li Nansheng Han Zhengxu Bakale Roger P Wald Stephen A |
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Affiliation: | Chemical Process Research and Development, Sepracor, Inc., 84 Waterford Drive, Marlborough, Massachusetts 01752, USA. zlu@rdg.boehringer-ingelheim.com |
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Abstract: | [reaction: see text] An efficient method has been developed to prepare all four isomers of the hydroxyl derivatives of sibutramine by addition of Grignard reagents (R)- or (S)-5 to a single enantiomer of sulfinyl imine (R)-1 simply by tuning the reaction solvent. The phenomenon of the reversed diastereoselectivity in CH(2)Cl(2) and THF implied that the reaction may proceed through a chelated cyclic transition state in CH(2)Cl(2) and nonchelated acyclic transition state in THF. |
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