Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective 1,4-Conjugate Addition of β-Ketoesters to Nitroolefins

被引：5

作者：

Zhang, Hui ^{[1
,2
]}

Cun, Lin-Feng ^{[1
]}

Zhang, Xiao-Mei ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Sichuan Prov, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

LETTERS IN ORGANIC CHEMISTRY | 2010年 / 7卷 / 03期

基金：

中国国家自然科学基金;

关键词：

Chiral phosphoric acid; organocatalysis; asymmetric catalysis; 1,4-conjugate addition; beta-ketoesters; nitroolefins; MANNICH-TYPE REACTION; ASYMMETRIC CONJUGATE ADDITION; FRIEDEL-CRAFTS ALKYLATION; DIELS-ALDER REACTION; BRONSTED ACID; MICHAEL ADDITIONS; 1,3-DICARBONYL COMPOUNDS; ACYCLIC NITROALKENES; ORGANOBORONIC ACIDS; KETONES;

D O I：

10.2174/157017810791112360

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral phosphoric acid as organocatalyst for the diastereo- and enantioselectivity 1,4-conjugate addition of a variety of beta-ketoesters to nitroolefins was firstly developed, providing the corresponding adducts in high yield (up to 97%) with moderate diastereoselectivities (up to 2.6:1 dr) and enantioselectivities (up to 58% ee).

引用

页码：219 / 225

页数：7

共 65 条

[1] Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL [J].

Akiyama, T ;

Saitoh, Y ;

Morita, H ;

Fuchibe, K .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1523-1526

[2] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].

Akiyama, T ;

Morita, H ;

Itoh, J ;

Fuchibe, K .

ORGANIC LETTERS, 2005, 7 (13) :2583-2585

[3] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[4] Vinylogous Mannich-type reaction catalyzed by an iodine-substituted chiral phosphoric acid [J].

Akiyama, Takahiko ;

Honma, Yasuhiro ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :399-402

[5] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[6] Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction [J].

Akiyama, Takahiko ;

Morita, Hisashi ;

Fuchibe, Kohei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13070-13071

[7] Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions [J].

Alexakis, A ;

Benhaim, C ;

Rosse, S ;

Humam, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5262-5263

[8] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine [J].

Andrey, O ;

Alexakis, A ;

Bernardinelli, G .

ORGANIC LETTERS, 2003, 5 (14) :2559-2561

[9] Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram [J].

Barnes, DM ;

Ji, JG ;

Fickes, MG ;

Fitzgerald, MA ;

King, SA ;

Morton, HE ;

Plagge, FA ;

Preskill, M ;

Wagaw, SH ;

Wittenberger, SJ ;

Zhang, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13097-13105

[10]

Barrett A.G. M., 1988, TETRAHEDRON LETT, V29, P5733, DOI DOI 10.1016/S0040-4039(00)82175-9

← 1 2 3 4 5 6 7 →