Conversion of serine. beta.-lactones to chiral. alpha.-amino acids by copper-containing organolithium and organomagnesium reagents

LD Arnold, JCG Drover, JC Vederas

Index: Arnold, Lee D.; Drover, John C. G.; Vederas, John C. Journal of the American Chemical Society, 1987 , vol. 109, # 15 p. 4649 - 4659

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Citation Number: 120

Abstract

Abstract: A method for synthesis of optically pure a-amino acids has been developed. Mono- and di-N-protected a-amino-@-lactones 3a (L, R,= H, R2= COOCH2Ph (Z)), 3b (D, R1= H, R2= Z), 3c (L, R,= CH2Ph, R2= Z), and 3d (D, RI= CH, Ph, R2= Z) are readily produced by cyclization of the corresponding serine derivatives 2 under modified Mitsunobu conditions without loss of optical purity. Stereochemical integrity was demonstrated by conversion of ...