Enantioselective α-Alkylation of Benzylideneamino tert-Butyl Malonates by Phase-Transfer Catalysis

被引：10

作者：

Park, Cheonhyoung ^{[1
,2
]}

Ha, Min Woo ^{[1
,2
]}

Kim, Byungsoo ^{[1
,2
]}

Hong, Suckchang ^{[1
,2
]}

Kim, Doyoung ^{[1
,2
]}

Park, Yohan ^{[3
]}

Kim, Mi-hyun ^{[4
]}

Lee, Jae Kyun ^{[5
]}

Lee, Jeeyeon ^{[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

[4] Gachon Univ, Coll Pharm, Inchon 406799, South Korea

[5] Korea Inst Sci & Technol, Neuromed Ctr, Seoul 130650, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 13期

基金：

新加坡国家研究基金会;

关键词：

asymmetric synthesis; alpha; alpha-dialkylmalonates; enantioselectivity; phase-transfer catalysis; PTC; ASYMMETRIC ALKYLATION; STEREOSELECTIVE-SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITION; MICHAEL ADDITIONS; CARBON CENTER; AMINO-ACIDS; CONSTRUCTION; DESYMMETRIZATION; FLUORINATION;

D O I：

10.1002/adsc.201500560

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new enantioselective synthetic method for the synthesis of alpha,alpha-dialkylmalonates with a quaternary carbon center was developed via alpha-alkylation of prochiral malonates by phase-transfer catalysis (PTC). Asymmetric alpha-alkylation of benzylideneamino tert-butyl alpha-methylmalonates under phase-transfer catalytic conditions in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded the corresponding alpha,alpha-dialkylmalonates in high yields (up to 97%) with excellent enantioselectivities (up to 98% ee). The products were then selectively hydrolyzed to chiral malonic monoacids under basic, acidic, or catalytic hydrogenation conditions.

引用

页码：2841 / 2848

页数：8

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