. alpha.-Amino acids as chiral educts for asymmetric products. A general synthesis of D-. alpha.-amino acids from L-serine

PJ Maurer, H Takahata, H Rapoport

Index: Maurer; Takahata; Rapoport Journal of the American Chemical Society, 1984 , vol. 106, # 4 p. 1095 - 1098

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Citation Number: 90

Abstract

Abstract: A short and chirally efficient synthesis of four Da-amino acids is described with L- serine as the chiral educt. The key CC bond-forming reactions are the aminoacylations of organometallics with the lithium salt of N-(phenylsulfony1)-L-serine (2) to give optically pure N-blocked a-amino ketones. Reduction of the carbonyl group to carbinol or methylene followed by oxidation of the hydroxymethyl to carboxyl gives the N-blocked n-amino acids. ...