Syn-Selective Synthesis of β-Branched α-Amino Acids by Alkylation of Glycine-Derived Imines with Secondary Sulfonates

被引：10
|
作者：
Lou, Sha [1 ]
McKenna, Grace M. [1 ]
Tymonko, Steven A. [1 ]
Ramirez, Antonio [1 ]
Benkovics, Tamas [1 ]
Conlon, David A. [1 ]
Gonzalez-Bobes, Francisco [1 ]
机构：
[1] Bristol Myers Squibb Co, Chem Dev, New Brunswick, NJ 08903 USA
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 20期
关键词：
PAIR S(N)2 REACTIONS; ASYMMETRIC-SYNTHESIS; MANNICH REACTION; HALIPEPTIN-A; DAPTOMYCIN; BIOSYNTHESIS; DERIVATIVES; CYCLIZATION; LITHIUM; SODIUM;
D O I：
10.1021/acs.orglett.5b02448
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A syn-selective synthesis of beta-branched alpha-amino acids has been developed based on the alkylation of glycine imine esters with secondary sulfonates. The potassium counterion for the enolate, the solvent, and the leaving group on the electrophile were key levers to maximize the diasteroselectivity of the alkylation. The optimized conditions enabled a straightforward preparation of a number of beta-branched alpha-amino acids that can be challenging to obtain.
引用
收藏
页码：5000 / 5003
页数：4
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