SYNTHESIS OF NONPROTEINOGENIC AMINO ACIDS PART 2: PREPARATION OF A SYNTHETIC EQUIVALENT OF THE γ-ANION SYNTHON FOR ASYMMETRIC AMINO ACID SYNTHESIS
The synthesis of α-t-butyl γ-methyl N-trityl-(S)-glutamate (12) from (S)-glutamic acid (6) is described.Diester (12), on treatment with lithium isopropylcyclohexylamide followed by the addition of carbonyl compounds, reacts to give the γ-substituted glutamic acid derivatives (13a-i) with retention of optical purity at the α centre.
Baldwin, Jack E.,North, Michael,Flinn, Anthony,Moloney, Mark G.
p. 1453 - 1464
(2007/10/02)
Stereospecific Amino Acid Synthesis; Preparation of the γ-Anion derived from Glutamic Acid
Reaction of α-t-butyl γ-methyl N-trityl-L-glutamate (7) with lithium isopropylcyclohexylamide in hexane leads to the specific formation of the γ-ester enolate, a potential synthetic equivalent to the γ-anion synthon for stereospecific α-amino acid synthesis.
Baldwin, Jack E.,North, Michael,Flinn, Anthony,Moloney, Mark G.
p. 828 - 829
(2007/10/02)
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