Asymmetric Cyclization Reactions of Allenoates with Imines or α,β-Unsaturated Ketones Catalyzed by Organocatalysts Derived from Cinchona Alkaloids

被引：44

作者：

Pei, Cheng-Kui ^{[3
]}

Shi, Min ^{[1
,2
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 22期

基金：

中国国家自然科学基金;

关键词：

allenoates; asymmetric catalysis; cinchona alkaloids; cyclization; organocatalysis; ELECTRON-DEFICIENT OLEFINS; BAYLIS-HILLMAN REACTIONS; ONE-POT SYNTHESIS; ALLENIC ESTERS; 4+2 ANNULATION; ENANTIOSELECTIVE SYNTHESIS; ETHYL 2,3-BUTADIENOATE; 3+2 CYCLOADDITION; CLAISEN REARRANGEMENT; PHOSPHINE CATALYSIS;

D O I：

10.1002/chem.201200209

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lewis base-catalyzed cyclization reactions of allenoates with electron-deficient olefins and imines have been demonstrated by the preparation of biologically active natural products and pharmaceutically interesting substances and have emerged as powerful synthetic tools in the rapid construction of cyclic molecular complexity. In contrast to phosphine-containing Lewis bases, nitrogen-containing Lewis base amines display markedly different reaction profiles; however, this area is not well-developed. Herein we summarize the recent progress in this emerging field and outline the challenges ahead.

引用

页码：6712 / 6716

页数：5

共 62 条

[11] Cinchona Alkaloid Amide Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Synthesis of 2,4-Disubstituted Azetidines [J].

Denis, Jean-Baptiste ;

Masson, Geraldine ;

Retailleau, Pascal ;

Zhu, Jieping .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (23) :5356-5360

[12] A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol [J].

Du, YS ;

Lu, XY .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6463-6465

[13] Highly regioselective construction of spirocycles via phosphine-catalyzed [3+2]-cycloaddition [J].

Du, YS ;

Lu, XY ;

Yu, YH .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8901-8905

[14] Theoretical rationale for regioselection in phosphine-catalyzed allenoate additions to acrylates, imines, and aldehydes [J].

Dudding, Travis ;

Kwon, Ohyun ;

Mercier, Evan .

ORGANIC LETTERS, 2006, 8 (17) :3643-3646

[15] Diversity-generation from an allenoate-enone coupling: syntheses of azepines and pyrimidones from common precursors [J].

Evans, CA ;

Cowen, BJ ;

Miller, SJ .

TETRAHEDRON, 2005, 61 (26) :6309-6314

[16] Amine-catalyzed coupling of allenic esters to α,β-unsaturated carbonyls [J].

Evans, CA ;

Miller, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12394-12395

[17] Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3+2] cycloadditions [J].

Fang, Yuan-Qing ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5660-+

[18] Beyond the Aza-Morita-Baylis-Hillman Reaction: Lewis Base-Catalyzed Reactions of N-Boc-imines with Ethyl 2,3-Butadienoate [J].

Guan, Xiao-Yang ;

Wei, Yin ;

Shi, Min .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :6343-6346

[19] Enantioselective [3+2] Cycloaddition of Allenes to Acrylates Catalyzed by Dipeptide-Derived Phosphines: Facile Creation of Functionalized Cyclopentenes Containing Quaternary Stereogenic Centers [J].

Han, Xiaoyu ;

Wang, Youqing ;

Zhong, Fangrui ;

Lu, Yixin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) :1726-1729

[20]

Lang R.W., 1984, ORG SYNTH, V62, P202

← 1 2 3 4 5 6 7 →