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Synthesis of α,α‐Difluoro‐β‐amino Esters or gem ‐Difluoro‐β‐lactams as Potential Metallocarboxypeptidase Inhibitors
Author(s) -
Boyer Nicolas,
Gloanec Philippe,
De Nanteuil Guillaume,
Jubault Philippe,
Quirion JeanCharles
Publication year - 2008
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.200800363
Subject(s) - chemistry , acylation , alkylation , lactam , stereochemistry , amino acid , combinatorial chemistry , organic chemistry , catalysis , biochemistry
The synthesis of gem ‐difluorinated β‐lactams and gem ‐difluorinated β‐amino acids, each possessing a potential basic functional group, from ethyl bromodifluoroacetate and either imines (for β‐lactams) or N ‐(α‐aminoalkyl)benzotriazoles (for β‐amino esters) was investigated. A series of these compounds were used for the design of novel metallocarboxypeptidase inhibitors. N ‐Alkylation and N ‐acylation of these two versatile scaffolds were carried out, leading to the expected targets in moderate to good yields.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)