Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines: An Umpolung Strategy

被引：135

作者：

Hashimoto, Takuya ^{[1
]}

Omote, Masato ^{[1
]}

Maruoka, Keiji ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 15期

关键词：

Bronsted acids; carboxylic acid; cycloadditions; organocatalysis; umpolung; CHIRAL DICARBOXYLIC-ACID; N-BOC IMINES; LEWIS-ACID; ENANTIOSELECTIVE ADDITION; TERMINAL ALKYNES; NITRONES; N; N-DIALKYLHYDRAZONES; N-DIMETHYLHYDRAZONES; CONSTRUCTION; ALDEHYDES;

D O I：

10.1002/anie.201100331

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oompa loompa: The title reaction has been accomplished with high stereoselectivity by use of an axially chiral dicarboxylic acid (see scheme). Employment of vinylogous aza-enamines as novel dipolarophiles was also implemented to establish a new concept of the inverse-electron-demand umpolung 1,3-dipolar cycloaddition. Bz=benzoyl, EDG=electron-donating group. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3489 / 3492

页数：4

共 51 条

[1] Stronger bronsted acids [J].

Akiyama, Takahiko .

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

[2]

[Anonymous], 2005, ANGEW CHEM-GER EDIT

[3] Ruthenium Lewis Acid Catalyzed Asymmetric 1,3-Dipolar Cycloadditions between N-Methylnitrones and Enals [J].

Badoiu, Andrei ;

Bernardinelli, Gerald ;

Kuendig, E. Peter .

SYNTHESIS-STUTTGART, 2010, (13) :2207-2212

[4] Aldehyde N,N-dialkylhydrazones as neutral acyl anion equivalents:: Umpolung of the imine reactivity [J].

Brehme, Rainer ;

Enders, Dieter ;

Fernandez, Rosario ;

Lassaletta, Jose M. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (34) :5629-5660

[5]

Chen W., 2007, ANGEW CHEM, V119, P7811

[6] Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: Beneficial effects of hydrogen bonding [J].

Chen, Wei ;

Du, Wei ;

Duan, Yong-Zheng ;

Wu, Yong ;

Yang, Sheng-Yong ;

Chen, Ying-Chun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (40) :7667-7670

[7] Organocatalytic and stereoselective [3+2] cycloadditions of azomethine imines with α,β-unsaturated aldehydes [J].

Chen, Wei ;

Yuan, Xiang-Hong ;

Li, Rui ;

Du, Wei ;

Wu, Yong ;

Ding, Li-Sheng ;

Chen, Ying-Chun .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) :1818-1822

[8] Asymmetric organocatalytic three-component 1,3-dipolar cycloaddition: Control of stereochemistry via a chiral bronsted acid activated dipole [J].

Chen, Xiao-Hua ;

Zhang, Wen-Quan ;

Gong, Liu-Zhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5652-+

[9] Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity [J].

Chen, Xiao-Hua ;

Wei, Qiang ;

Luo, Shi-Wei ;

Xiao, Han ;

Gong, Liu-Zhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) :13819-13825

[10] Mechanistic studies on the catalytic asymmetric Mannich-type reaction with dihydroisoquinolines and development of oxidative Mannich-type reactions starting from tetrahydroisoquinolines [J].

Dubs, Christian ;

Hamashima, Yoshitaka ;

Sasamoto, Naoki ;

Seidel, Thomas M. ;

Suzuki, Shoko ;

Hashizume, Daisuke ;

Sodeoka, Mikiko .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) :5859-5871

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