Bifunctional N-Acyl-Aminophosphine-Catalyzed Asymmetric [4+2] Cycloadditions of Allenoates and Imines

被引：99

作者：

Xiao, Hua ^{[1
]}

Chai, Zhuo ^{[2
]}

Wang, Hai-Feng ^{[2
]}

Wang, Xiao-Wei ^{[2
]}

Cao, Dong-Dong ^{[1
]}

Liu, Wen ^{[1
]}

Lu, Ying-Peng ^{[2
]}

Yang, Ying-Quan ^{[1
]}

Zhao, Gang ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Modern Synthet Chem, Shanghai 200032, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 38期

基金：

中国国家自然科学基金;

关键词：

aminophosphines; asymmetric catalysis; bifunctional catalyst; cycloaddition; organocatalysis; HIGHLY FUNCTIONALIZED TETRAHYDROPYRIDINES; ELECTRON-DEFICIENT OLEFINS; MODIFIED ALLYLIC COMPOUNDS; PHOSPHORUS YLIDE REACTION; BAYLIS-HILLMAN REACTIONS; DIELS-ALDER REACTIONS; 3+2 ANNULATION; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; PHOSPHINE ORGANOCATALYSIS;

D O I：

10.1002/chem.201100850

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Try bifunctional aminophosphines! An asymmetric organocatalytic [4+2] cycloaddition between α-substituted allenoates and tosylaldimines using bifunctional N-acyl aminophosphine catalysts was described (see scheme). This operationally simple catalytic system could provide valuable complementary results to those of the monodentate phosphine system. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10562 / 10565

页数：4

共 91 条

[31] Asymmetric Total Synthesis of the Iridoid β-Glucoside (+)-Geniposide via Phosphine Organocatalysis [J].

Jones, Regan A. ;

Krische, Michael J. .

ORGANIC LETTERS, 2009, 11 (08) :1849-1851

[32]

Jorgensen K. A., 2000, ANGEW CHEM, V112, P3702, DOI DOI 10.1002/1521-3757(20001016)112:20<3702::AID-ANGE3702>3.0.CO

[33]

2-R

[34]

Jorgensen KA, 2000, ANGEW CHEM INT EDIT, V39, P3558, DOI 10.1002/1521-3773(20001016)39:20<3558::AID-ANIE3558>3.0.CO

[35]

2-I

[36] Development of a one-pot asymmetric azaelectrocyclization protocol: Synthesis of chiral 2,4-disubstituted 1,2,5,6-tetrahydropyridines [J].

Kobayashi, Toyoharu ;

Nakashima, Miyuki ;

Hakogi, Toshikazu ;

Tanaka, Katsunori ;

Katsumura, Shigeo .

ORGANIC LETTERS, 2006, 8 (17) :3809-3812

[37] Enantioselective synthesis of a chiral fluoropiperidine via asymmetric hydrogenation of a vinyl fluoride [J].

Krska, Shane W. ;

Mitten, Jeffrey V. ;

Dormer, Peter G. ;

Mowrey, Dale ;

Machrouhi, Fouzia ;

Sun, Yongkui ;

Nelson, Todd D. .

TETRAHEDRON, 2009, 65 (44) :8987-8994

[38] Unusual [8+2] annelation in the reactions of allenic ester/ketone-derived 1,3-dipoles with tropone [J].

Kumar, K ;

Kapur, A ;

Ishar, MPS .

ORGANIC LETTERS, 2000, 2 (06) :787-789

[39] Stereoselective Synthesis of 2,3,6-Trisubstituted Tetrahydropyridines via Tf2O-Mediated Grob Fragmentation: Access to Indolizidines (-)-2091 and (-)-223J [J].

Lemonnier, Gerald ;

Charette, Andre B. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21) :7465-7467

[40] Mechanism, regioselectivity, and the kinetics of phosphine-catalyzed [3+2] cycloaddition reactions of allenoates and electron-deficient alkenes [J].

Liang, Yong ;

Liu, Song ;

Xia, Yuanzhi ;

Li, Yahong ;

Yu, Zhi-Xiang .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (14) :4361-4373

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