Phosphine-Catalyzed [3+2] Annulation of γ- Substituted Allenoates: Novel Access to Functionalized Cyclopentenes and Bicyclic[3,3,0]octene Derivatives

被引：24

作者：

Li, Erqing ^{[1
,2
,3
]}

Jin, Hongxing ^{[1
,2
]}

Huang, You ^{[1
,2
,4
]}

机构：

[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China

[2] Nankai Univ, Coll Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

[3] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China

[4] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

来源：

CHEMISTRYSELECT | 2018年 / 3卷 / 42期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

organocatalysis; allenoates; domino reaction; cyclopenetens; bicyclic compounds; UMPOLUNG ADDITION; DOMINO REACTION; BASE CATALYSIS; SEQUENTIAL 2+3; FACILE ACCESS; CYCLOADDITION; CONSTRUCT; ALLENES; IMINES; 2,3-BUTADIENOATES;

D O I：

10.1002/slct.201802800

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The phosphine-catalyzed [3 + 2] cyclizations of gamma-substituted allenoates have been applied to the synthesis of functionalized cyclopentenes and bicyclic compounds in moderate to good yields. The operation is simple and scalable with good functional group tolerance. In addition, the novel substrate-controlled phosphine-catalyzed domino reaction not only enriches the chemistry of gamma-substituted allenoates, but also enables easy access to skeletally diverse products.

引用

页码：12007 / 12010

页数：4

共 66 条

[1] Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3+2] annulation [J].

Andrews, Ian P. ;

Kwon, Ohyun .

CHEMICAL SCIENCE, 2012, 3 (08) :2510-2514

[2]

[Anonymous], 2015, ANGEW CHEM

[3]

[Anonymous], 2010, ANGEW CHEM, DOI DOI 10.1002/ANGE.201000446

[4] The Rauhut-Currier reaction: a history and its synthetic application [J].

Aroyan, Carrie E. ;

Dermenci, Alpay ;

Miller, Scott J. .

TETRAHEDRON, 2009, 65 (21) :4069-4084

[5] ANALOGS OF OXYBUTYNIN - SYNTHESIS AND ANTIMUSCARINIC AND BLADDER ACTIVITY OF SOME SUBSTITUTED 7-AMINO-1-HYDROXY-5-HEPTYN-2-ONES AND RELATED-COMPOUNDS [J].

CARTER, JP ;

NORONHABLOB, L ;

AUDIA, VH ;

DUPONT, AC ;

MCPHERSON, DW ;

NATALIE, KJ ;

RZESZOTARSKI, WJ ;

SPAGNUOLO, CJ ;

WAID, PP ;

KAISER, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (10) :3065-3074

[6] Enantioselective catalysis and complexity generation from allenoates [J].

Cowen, Bryan J. ;

Miller, Scott J. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3102-3116

[7] Alcohol-assisted phosphine catalysis: One-step syntheses of dihydropyrones from aldehydes and allenoates [J].

Creech, Gardner S. ;

Kwon, Ohyun .

ORGANIC LETTERS, 2008, 10 (03) :429-432

[8]

Denmark S.E., 2008, ANGEW CHEM, V120, P1584

[9] Lewis base catalysis in organic synthesis [J].

Denmark, Scott E. ;

Beutner, Gregory L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) :1560-1638

[10] 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

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