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

页码：4030 / 4039

页数：10

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