Catalytic Efficiency of Primary -Amino Alcohols and Their Derivatives in Organocatalysis

被引：51

作者：

Reddy, Ummareddy Venkata Subba ^{[1
]}

Chennapuram, Madhu ^{[1
]}

Seki, Chigusa ^{[1
]}

Kwon, Eunsang ^{[2
]}

Okuyama, Yuko ^{[3
]}

Nakano, Hiroto ^{[1
]}

机构：

[1] Muroran Inst Technol, Grad Sch Engn, Synthet Organ Chem Lab, Dept Bioengn, 27-1 Mizumoto, Muroran, Hokkaido 0508585, Japan

[2] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Aoba Ku, 6-3 Aoba, Sendai, Miyagi 9808578, Japan

[3] Tohoku Pharmaceut Univ, Aoba Ku, 4-4-1 Komatsushima, Sendai, Miyagi 9818558, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 24期

基金：

日本科学技术振兴机构;

关键词：

Organocatalysis; Asymmetric synthesis; C-C coupling; Amino alcohols; DIELS-ALDER REACTION; DIRECT ALDOL REACTIONS; ASYMMETRIC MICHAEL ADDITION; BAYLIS-HILLMAN REACTION; ENANTIOSELECTIVE EPOXIDATION; SYNTHETIC METHODOLOGY; DIETHYLZINC ADDITION; ACID CATALYST; D-GLUCOSAMINE; C-C;

D O I：

10.1002/ejoc.201600164

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral primary -amino alcohols, constuting adjacently positioned BrOnsted base and BrOnsted acid sites, are emerging as very valuable bifunctional organocatalysts in a wide array of asymmetric organic transformations. Primary -amino alcohols represent inexpensive alternatives to other primary amino organocatalysts such as chiral diamines and cinchona-alkaloid-derived primary amines, being easy to synthesize and air-stable and offering the potential for introduction of different functional groups and also for alteration of steric sites. Here we reveal the catalytic use of simple primary -amino alcohols and their derivatives as organocatalysts in Diels-Alder cycloaddition, aldol condensation, Michael addition, 1,3-dipolar cycloaddition, the Morita-Baylis-Hillman reaction, cascade cyclization, allylation of isatins, Friedel-Crafts alkylation and epoxidation of olefins.

引用

页码：4124 / 4143

页数：20

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