A simple and efficient diastereoselective Strecker synthesis of optically pure α-arylglycines
1999; Elsevier BV; Volume: 55; Issue: 37 Linguagem: Inglês
10.1016/s0040-4020(99)00673-0
ISSN1464-5416
Autores Tópico(s)Carbohydrate Chemistry and Synthesis
ResumoA simple and economical method for the synthesis of highly functionalised α-amino nitriles, precursors to α-arylglycines with high optical purity is reported. For this purpose, (R) or (S)-2-amino-2-phenylethanol were used as chiral auxiliaries in a 1,3 Strecker reaction. Reactions were studied with a broad range of reagent systems for the generation of cyano nucleophile. Methodology has been extended for the synthesis of (S)-α-(2-iodo-5-nitrophenyl)glycine, (S)-α-(4-methoxyphenyl)glycine and (R)-β-(4-methoxyphenyl)alanine.
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