Amide-Phosphonium Salt as Bifunctional Phase Transfer Catalyst for Asymmetric 1,6-Addition of Malonate Esters to para-Quinone Methides

被引：92

作者：

Ge, Luo ^{[1
]}

Lu, Xuehe ^{[1
]}

Cheng, Cang ^{[1
]}

Chen, Jie ^{[1
]}

Cao, Weiguo ^{[1
]}

Wu, Xiaoyu ^{[1
,2
]}

Zhao, Gang ^{[2
]}

机构：

[1] Shanghai Univ, Dept Chem, 99 Shangda Rd, Shanghai 200411, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, 354 Fenglin Lu, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 19期

基金：

中国国家自然科学基金;

关键词：

1,6-CONJUGATE ADDITION; AMINO-ACID; NUCLEOPHILIC REACTIVITIES; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; QUATERNARY CENTERS; EXPEDIENT ACCESS; QUANTIFICATION; OXINDOLES; ALDEHYDES;

D O I：

10.1021/acs.joc.6b01906

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric 1,6-addition of malonates to para-quinone methides has been developed by using amidephosphonium salts derived from easily available chiral alpha-amino acids as bifunctional phase transfer catalysts. Stabilized para-quinone methides with various substituents on the phenyl ring were reacted with diphenyl malonates to give functionalized diaryl methines in excellent yields and high to excellent ee's. Furthermore, to show the utility of this methodology, a gram scale synthesis of an 1,6-addition adduct and its further elaboration into the key intermediate for synthesis of GPR40 agonists were also described.

引用

页码：9315 / 9325

页数：11

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