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Norstatines from Aldehydes by Sequential Organocatalytic α‐Amination and Passerini Reaction
Author(s) -
Umbreen Sumaira,
Brockhaus Manfred,
Ehrenberg Helmut,
Schmidt Boris
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600502
Subject(s) - chemistry , peptidomimetic , amination , enantioselective synthesis , cleavage (geology) , organocatalysis , reductive amination , combinatorial chemistry , bond cleavage , organic chemistry , catalysis , peptide , biochemistry , geotechnical engineering , fracture (geology) , engineering
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)