Memory of Chirality of Tertiary Aromatic Amide: Application to the Asymmetric Synthesis of (S)-α-MethylDOPA
…, D Gori, C Kouklovsky, V Alezra
Index: Cam, Thuy Hoang; Bouillere, Francelin; Johannesen, Sine; Zulauf, Anais; Panel, Cecilia; Pouilhes, Annie; Gori, Didier; Alezra, Valerie; Kouklovsky, Cyrille Journal of Organic Chemistry, 2009 , vol. 74, # 11 p. 4177 - 4187
Full Text: HTML
Citation Number: 6
Abstract
We describe an original asymmetric synthesis of (S)-α-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)-α-methylDOPA hydrochloride is obtained after four steps with 98% ee.
Related Articles:
Unexpected conversion of alkyl azides to alkyl iodides and of aryl azides to N-tert-butyl anilines
[Maury, Julien; Feray, Laurence; Bertrand, Michele P.; Kapat, Ajoy; Renaud, Philippe Tetrahedron, 2012 , vol. 68, # 47 p. 9606 - 9611,6]
A new synthesis of fused 1, 2, 4-triazine derivatives
[Synthesis, , # 10 p. 853 - 854]
A new synthesis of fused 1, 2, 4-triazine derivatives
[Synthesis, , # 10 p. 853 - 854]
[Journal of Organic Chemistry, , vol. 66, # 11 p. 4006 - 4011]
[Journal of Organic Chemistry, , vol. 64, # 11 p. 3821 - 3824]