Premium
Design and Synthesis of Optically Active Esters of γ‐Amino‐β‐oxo Acids as Precursors for the Synthesis of Tetramic Acids Derived from L ‐Serine, L ‐Tyrosine, and L ‐Threonine
Author(s) -
Matiadis Dimitris,
IgglessiMarkopoulou Olga
Publication year - 2010
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.201000700
Subject(s) - chemistry , enantiomer , acylation , amino acid , methylene , optically active , threonine , serine , enantiomeric excess , organic chemistry , protecting group , stereochemistry , enantioselective synthesis , catalysis , biochemistry , enzyme , alkyl
Tetramic acids bearing a hydroxyalkyl or hydroxybenzyl group at C‐5 of the heterocyclic ring were successfully prepared. α‐Amino acids appropriately protected and activated were used as acylating agents for the C‐acylation of active methylene compounds. These novel synthesized intermediates, substituted γ‐amino acids, were isolated in excellent yields and enantiomeric purities. Cyclization under basic conditions afforded the desired products in high yields and enantiomeric purity.