Enantioselective direct Mannich reaction of functionalized acetonitrile to N-Boc imines catalyzed by quaternary phosphonium catalysis

被引：23

作者：

Pan, Renming ^{[1
]}

Zhang, Jiaxing ^{[2
]}

Zheng, Changwu ^{[2
]}

Wang, Hongyu ^{[2
]}

Cao, Dongdong ^{[2
]}

Cao, Weiguo ^{[1
]}

Zhao, Gang ^{[2
]}

机构：

[1] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2017年 / 73卷 / 17期

基金：

中国国家自然科学基金;

关键词：

Asymmetric Mannich reaction; Dual-reagent catalysis; Quaternary phosphonium; Organocatalysis; DUAL-REAGENT CATALYSIS; 3-SUBSTITUTED OXINDOLES; ACYL AMINOPHOSPHINES; 4+2 CYCLOADDITIONS; MICHAEL ADDITION; BENZYL NITRILES; AMINO-ACIDS; PHOSPHINE; ACTIVATION; ALLENOATES;

D O I：

10.1016/j.tet.2017.03.005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Quaternary phosphonium ion-pair or a salt derived from amino acid has been developed to catalyze the Mannich-type reaction of alpha-substituted ethyl cyanoacetates and 2-(2-nitrophenyl) acetonitrile to N-Boc imines. Experiments shown that more active cyanoacetates could be catalyzed by the gentle phosphonium ion-pair catalysis, while 2-(2-nitrophenyl) acetonitrile as the substrate has to be activated by quaternary phosphonium salts and strong base. All the reactions gave the corresponding highly functionalized chiral (beta-amino nitrites products with good yields, high diastereo-and enantioselectivities in mild conditions. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2349 / 2358

页数：10

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