Organocatalytic Synthesis of Spirocarbocycles

被引：12

作者：

Chong, You-Song ^{[1
]}

Anwar, Shaik ^{[2
]}

Chen, Kwunmin ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, 88 Sec 4,Tingchow Rd, Taipei 11677, Taiwan

[2] Vignans Fdn Sci Technol & Res, Dept Sci & Humanities, Div Chem, Guntur, Andhra Pradesh, India

来源：

MINI-REVIEWS IN ORGANIC CHEMISTRY | 2018年 / 15卷 / 05期

关键词：

C-C bonds; organocatalytic; cascade reaction; tandem strategies; spirocarbocycles; enantioselectivity; DIELS-ALDER REACTION; QUATERNARY CARBON CENTERS; DIARYLPROLINOL SILYL ETHERS; MICHAEL-ALDOL REACTION; CASCADE REACTIONS; ASYMMETRIC ORGANOCATALYSIS; CYCLOADDITION REACTIONS; DOMINO REACTIONS; SUBSTITUTED DISPIROCYCLOHEXANES; SPIROCYCLIC BENZOFURAN-2-ONES;

D O I：

10.2174/1570193X15666171228145726

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficient construction of C-C bonds with multiple stereocenters has been of synthetic interest to the synthetic community. This review describes the organocatalytic cascade, domino or tandem synthesis of spirocarbocycles that evolved through the use of small organic catalysts. Spirocarbocycles are frequently observed in organic compounds in nature, and the formation of spirocarbocycles is vital in contemporary organic synthesis. These reactions proceed through the combination of enamine, iminium, dienamine, and trienamine modes of activation to construct multiple C-C bonds with newly generated stereogenic centers.

引用

页码：364 / 373

页数：10

共 78 条

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].

Ahrendt, KA ;

Borths, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244

[2] Highly Stereoselective Synthesis of Spiropyrazolones [J].

Alba, Andrea-Nekane R. ;

Zea, Alex ;

Valero, Guillem ;

Calbet, Teresa ;

Font-Bardia, Merce ;

Mazzanti, Andrea ;

Moyano, Albert ;

Rios, Ramon .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (07) :1318-1325

[3] Applications of asymmetric organocatalysis in medicinal chemistry [J].

Aleman, Jose ;

Cabrera, Silvia .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (02) :774-793

[4] Organocatalytic Synthesis of Substituted Spirocyclohexane Carbaldehydes via [4+2] Annulation Strategy between 2-Arylideneindane-1,3-diones and Glutaraldehyde [J].

Anwar, Shaik ;

Li, Shao Ming ;

Chen, Kwunmin .

ORGANIC LETTERS, 2014, 16 (11) :2993-2995

[5] Organocatalysis - Organocatalysis lost: Modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus [J].

Barbas, Carlos F., III .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) :42-47

[6] Organocatalysis-after the gold rush [J].

Bertelsen, Soren ;

Jorgensen, Karl Anker .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189

[7] A proline-catalyzed asymmetric Robinson annulation reaction [J].

Bui, T ;

Barbas, CF .

TETRAHEDRON LETTERS, 2000, 41 (36) :6951-6954

[8] Multiple approaches to enantiopure spirocyclic benzofuranones using organocatalytic cascade reactions [J].

Cassani, Carlo ;

Tian, Xu ;

Escudero-Adan, Eduardo C. ;

Melchiorre, Paolo .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :233-235

[9] Enantioselective Synthesis of Functionalized Polycarbocycles via a Three-Component Organocascade Quadruple Reaction [J].

Chang, Yun-Pu ;

Gurubrahamam, Ramani ;

Chen, Kwunmin .

ORGANIC LETTERS, 2015, 17 (12) :2908-2911

[10] Streocontrolled Construction of Six Vicinal Stereogenic Centers on Spiropyrazolones via Organocascade Michael/Michael/1,2-Addition Reactions [J].

Chauhan, Pankaj ;

Mahajan, Suruchi ;

Loh, Charles C. J. ;

Raabe, Gerhard ;

Enders, Dieter .

ORGANIC LETTERS, 2014, 16 (11) :2954-2957

← 1 2 3 4 5 6 7 8 →