Enantioselective phase-transfer catalytic α-alkylation of 2-methylbenzyl tert-butyl malonates

被引：10
|
作者：
Ha, Min Woo [1 ,2 ]
Hong, Suckchang [1 ,2 ]
Park, Cheonhyoung [1 ,2 ]
Park, Yohan [3 ]
Lee, Jihye [1 ,2 ]
Kim, Mi-Hyun [1 ,2 ]
Lee, Jihoon [1 ,2 ]
Park, Hyeung-Geun [1 ,2 ]
机构：
[1] Seoul Natl Univ, Pharmaceut Sci Res Inst, Seoul 151742, South Korea
[2] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea
[3] Inje Univ, Coll Pharm, Gimhae 621749, Gyeongnam, South Korea
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 24期
基金：
新加坡国家研究基金会;
关键词：
AMINO-ACIDS; ASYMMETRIC ALKYLATION; DESYMMETRIZATION; CONSTRUCTION;
D O I：
10.1039/c3ob40481a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new asymmetric synthetic method to prepare alpha,alpha-dialkylmalonates for the construction of a quaternary carbon center via phase-transfer catalytic (PTC) alkylation has been developed. Enantioselective alpha-alkylation of 2-methylbenzyl tert-butyl alpha-methylmalonates under phase-transfer catalytic conditions in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide (10) afforded the corresponding alpha,alpha-dialkylmalonates in high chemical (up to 99%) and optical yields (up to 91% ee), which were selectively hydrolyzed to malonic monoacids under alkali basic conditions for conversion to versatile chiral intermediates.
引用
收藏
页码：4030 / 4039
页数：10
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