Norstatines from Aldehydes by Sequential Organocatalytic α‐Amination and Passerini Reaction

Abstract

Abstract The combination of the enantioselective, organocatalytic α‐amination of aldehydes by diazodicarboxylates and the Passerini reaction provides rapid access to norstatine‐based peptidomimetics. These intermediates were elaborated further by deprotection and cleavage of the N–N bond to provide useful building blocks for aspartic protease inhibitors. Coupling of the compounds 76 – 86 with the mono‐isophthalamide 91 provided moderate inhibitors of human β‐secretase (BACE) 92 – 102 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)