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Diastereoselective Synthesis of α‐Methylpyroglutamates from α,β‐Didehydro α‐Amino Acids
Author(s) -
AlvarezIbarra Carlos,
Csákÿ Aurelio G.,
Oliva Cristina Gómez de la
Publication year - 2002
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 - 10.1002/1099-0690(200212)2002:24<4190::aid-ejoc4190>3.0.co;2-q
Subject(s) - chemistry , moiety , stereochemistry , ring (chemistry) , amino acid , combinatorial chemistry , organic chemistry , biochemistry
A new method for the diastereoselective synthesis of α‐methylpyroglutamates from α,β‐didehydro‐ N ‐(diphenylmethylene)glutamates has been developed. Deprotection of the (diphenylmethylene)amino moiety of the starting materials affords pyridazinone derivatives which can be transformed into α‐methyl‐6‐oxoperhydropyridazine‐3‐carboxylates in a highly diastereoselective fashion. Ring contraction of the latter induced by LiHMDS affords α‐methylpyroglutamates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002)