Tetrahedron Letters

Synthesis of α-amino acids by ring opening of aziridine-2-carboxylates with carbon nucleophiles

NJ Church, DW Young

Index: Church, Nicola J.; Young, Douglas W. Tetrahedron Letters, 1995 , vol. 36, # 1 p. 151 - 154

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Citation Number: 74

Abstract

Excellent regiospecificity has been achieved in the reaction of carbon nucleophiles with N- para-toluenesulfonylaziridine-2-carboxylic acid (6, R= H protected as the anion. This has been developed into a general and high yielding synthesis of optically pure α-amino acids containing one chiral centre. When the aziridine (20) containing a second chiral centre was used, only lithium trimethylsilylacetylide gave the desired α-amino acid. Reaction with ...

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