A novel crystallization-induced diastereomeric transformation based on a reversible carbon-sulfur bond formation. Application to the synthesis of a γ-secretase …

…, AD Gibb, DC Hammond, DR Lieberman…

文献索引：Davies, Antony J.; Scott, Jeremy P.; Bishop, Brian C.; Brands, Karel M. J.; Brewer, Sarah E.; DaSilva, Jimmy O.; Dormer, Peter G.; Dolling, Ulf-H.; Gibb, Andrew D.; Hammond, Deborah C.; Lieberman, David R.; Palucki, Michael; Payack, Joseph F. Journal of Organic Chemistry, 2007 , vol. 72, # 13 p. 4864 - 4871

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被引用次数: 7

摘要

This paper describes a remarkably efficient process for the preparation of γ-secretase inhibitor 1. The target is synthesized in only five steps with an overall yield of 58%. The key operation is a highly selective and practical, crystallization-driven transformation for the conversion of a mixture of tertiary benzylic alcohols into the desired sulfide diastereomer with 94: 6 dr. This unprecedented process is based upon a reversible carbon-sulfur bond ...