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

被引：14

作者：

Thi Thoa Mai ^{[1
]}

Viswambharan, Baby ^{[1
]}

Gori, Didier ^{[1
]}

Kouklovsky, Cyrille ^{[1
]}

Alezra, Valerie ^{[1
]}

机构：

[1] Univ Paris 11, CNRS, Lab Chim Procedes & Subst Nat, ICMMO,UMR 8182, F-91405 Orsay, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 19期

关键词：

STEREOSELECTIVE-SYNTHESIS; AMINO-ACIDS; ENOLATE; (R)-ALPHA-METHYLDOPA; HOMOLOGATION; ALKYLATION; METHYLDOPA; ALDEHYDES; ROTATION; ACCESS;

D O I：

10.1021/jo301588t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：8797 / 8801

页数：5

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