A Novel Crystallization-Induced Diastereomeric TransformationBased on a Reversible Carbon−Sulfur Bond Formation. Applicationto the Synthesis of a γ-Secretase Inhibitor
This paper describes a remarkably efficient process for the preparation of γ-secretase inhibitor 1. Thetarget is synthesized in only five steps with an overall yield of 58%. The key operation is a highlyselective and practical, crystallization-driven transformation for the conversion of a mixture of tertiarybenzylic alcohols into the desired sulfide diastereomer with 94:6 dr. This unprecedented process is basedupon a reversible carbon−sulfur bond formation under acidic conditions.
