Organocatalyzed highly stereoselective Michael addition of ketones to alkylidene malonates and nitroolefins using chiral primary-secondary diamine catalysts based on bispidine

被引：57

作者：

Liu, Jie ^{[1
]}

Yang, Zhigang ^{[1
]}

Liu, Xiaohua ^{[1
]}

Wang, Zhen ^{[1
]}

Liu, Yanling ^{[1
]}

Bai, Sha ^{[1
]}

Lin, Lili ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 19期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC ALDOL REACTIONS; ENANTIOSELECTIVE CONJUGATE ADDITION; 1,3-DICARBONYL COMPOUNDS; ALDEHYDES; AMINE; THIOUREA; STEREOCENTERS; 1,4-ADDITION; ENONES;

D O I：

10.1039/b910939k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Organocatalysts containing primary-secondary diamines based on bispidine have been developed to catalyze the asymmetric Michael addition of ketones to alkylidene malonates and nitroalkenes. The corresponding products were obtained in high yields (up to 99%) with high diastereoselectivities (up to 99: 1) and high enantioselectivities (up to 97% ee) under mild conditions using either environmentally benign water as the solvent or no solvent.

引用

页码：4120 / 4127

页数：8

共 74 条

[41] Direct enantioselective Michael addition of aldehydes to vinyl ketones catalyzed by chiral amines [J].

Melchiorre, P ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4151-4157

[42] Asymmetric enamine catalysis [J].

Mukherjee, Santanu ;

Yang, Jung Woon ;

Hoffmann, Sebastian ;

List, Benjamin .

CHEMICAL REVIEWS, 2007, 107 (12) :5471-5569

[43] THE SYNTHESIS OF 1-BROMOBENZO [C]PHENANTHRENE [J].

NEWMAN, MS ;

PHILLIPS, DK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (14) :3667-3670

[44] SOME FACTORS INFLUENCING THE 1,4-ADDITION OF GRIGNARD REAGENTS TO ARYLIDENEMALONIC ESTERS [J].

NEWMAN, MS ;

FLANAGAN, HR .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (06) :796-797

[45] Highly efficient asymmetric Michael addition of aldehydes to nitroalkenes catalyzed by a simple trans-4-hydroxyprolylamide [J].

Palomo, Claudio ;

Vera, Silvia ;

Mielgo, Antonia ;

Gomez-Bengoa, Enrique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) :5984-5987

[46] Simple diamine- and triamine-protonic acid catalysts for the enantioselective Michael addition of cyclic ketones to nitroalkenes [J].

Pansare, Sunil V. ;

Pandya, Keyur .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9624-9625

[47] Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: Cocatalyst effects and evidence for an enamine intermediate [J].

Peelen, TJ ;

Chi, YG ;

Gellman, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11598-11599

[48]

Perlmutter P., 1992, In Conjugate Addition Reactions in Organic Synthesis

[49] Cyclohexane-1,2-diamines: Efficient Catalysts for the Enantioselective Conjugate Addition of Ketones to Nitro Olefins [J].

Rasappan, Ramesh ;

Reiser, Oliver .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (09) :1305-1308

[50] Amino acid catalyzed direct asymmetric aldol reactions: A bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions [J].

Sakthivel, K ;

Notz, W ;

Bui, T ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) :5260-5267

← 1 2 3 4 5 6 7 8 →