Journal of Organic Chemistry p. 5918 - 5924 (1993)
Update date:2022-08-04
Topics:
Colson, Pierre-Jean
Hegedus, Louis S.
Optically active bicyclic β-lactam 3 was synthesized by photolysis of optically active oxazolidine carbene chromium complex 1 with oxazine 2.Conversion of the oxazolidine to the oxazolidinone gave a bicyclic β-lactam readily α-alkylated.Cleavage of the alkylated β-lactam gave optically active ester aldehyde 7, which was converted to a number of optically active α-alkyl-α-amino acids.These include (R)-α-methylserine, (S)-α-methylglutamic acid, (S)-α-methylornithine, (S)-vinylalanine, (S)-ethynylalanine, and (S)-2-methyl-2,3-diaminopropionic acid.
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