Synthesis of chiral malonates by α-alkylation of 2,2-diphenylethyl tert-butyl malonates via enantioselective phase-transfer catalysis

Frontiers in Chemistry

Chemistry

Min Sagong¹  Daehyun Oh¹  Zhibin Guo¹  Jewon Yang¹  Geumwoo Lee²  Hyeung-geun Park³ 

[1] Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, Republic of Korea;[e-mail];null;

关键词: asymmetric synthesis;    phase-transfer catalysis;    enantioselective;    alkylation;    organocatalysis;   

DOI  :  10.3389/fchem.2023.1205661

 received in 2023-04-14, accepted in 2023-05-16,  发布年份 2023

来源: Frontiers

【 摘 要 】

An efficient synthetic approach for chiral malonates was established via enantioselective phase transfer catalysis. The α-alkylation of 2,2-diphenylethyl tert-butyl α-methylmalonates with (S,S)-3,4,5-trifluorophenyl-NAS bromide as a phase-transfer catalyst under phase-transfer catalytic conditions successfully produced corresponding α-methyl-α-alkylmalonates; these compounds are versatile chiral building blocks containing a quaternary carbon center in high chemical yields (up to 99%) with excellent enantioselectivities (up to 98% ee). α,α-Dialkylmalonates were selectively hydrolyzed to the corresponding chiral malonic monoacids under basic (KOH/MeOH) and acidic conditions (TFA/CH2Cl2), showing the practicality of the method.

【 授权许可】

Unknown   
Copyright © 2023 Guo, Oh, Sagong, Yang, Lee and Park.

【 图 表 】

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