Memory of Chirality of Tertiary Aromatic Amide: Application to the Asymmetric Synthesis of (S)-alpha-MethylDOPA

作者：Thi Thoa Mai; Viswambharan Baby; Gori Didier; Kouklovsky Cyrille; Alezra Valerie^*

来源：Journal of Organic Chemistry, 2012, 77(19): 8797-8801.

DOI：10.1021/jo301588t

We describe an original asymmetric synthesis of (S)-alpha-methylDOPA proceeding by the concept of memory of chirality, the only source of chirality being the starting D-alanine. The initial chirality of the amino acid is temporarily transferred to a dynamic axial chirality of a tertiary aromatic amide. The (S)-alpha-methylDOPA hydrochloride is obtained after four steps with 98% ee.

• 出版日期2012-10-5