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
收藏
页码：2841 / 2848
页数：8
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