Synthesis of Quaternary α-Methyl α-Amino Acids by Asymmetric Alkylation of Pseudoephenamine Alaninamide Pivaldimine

被引：24

作者：

Hugelshofer, Cedric L. ^{[1
]}

Mellem, Kevin T. ^{[1
]}

Myers, Andrew G. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 12期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; RECENT PROGRESS;

D O I：

10.1021/ol401337p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary alpha-methyl alpha-amino acids Is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide alpha-amino acids without salt contaminants. Alternatively, alpha-amino esters can be obtained by direct alcoholysis.

引用

页码：3134 / 3137

页数：4

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