863605-28-1Relevant articles and documents
A novel crystallization-induced diastereomeric transformation based on a reversible carbon-sulfur bond formation. Application to the synthesis of a γ-secretase inhibitor
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.
, p. 4864 - 4871 (2007)
(Chemical Equation Presented) 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 formation under acidic conditions.
