Synthesis of α-amino acids by ring opening of aziridine-2-carboxylates with carbon nucleophiles
1995; Elsevier BV; Volume: 36; Issue: 1 Linguagem: Inglês
10.1016/0040-4039(94)02198-k
ISSN1873-3581
AutoresNicola J. Church, Douglas W. Young,
Tópico(s)Synthesis and Catalytic Reactions
ResumoExcellent 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 higher order cuprates gave lower yields, the principal products being the protected β-amino acids (22) and (23).
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