Recent development in asymmetric organocatalytic domino reactions involving 1,6-addition as a key step

被引：34

作者：

Hussain, Yaseen ^{[1
]}

Tamanna ^{[1
]}

Sharma, Manisha ^{[1
]}

Kumar, Akshay ^{[2
]}

Chauhan, Pankaj ^{[1
]}

机构：

[1] Indian Inst Technol Jammu, Dept Chem, NH-44, Jammu 181221, Jammu & Kashmir, India

[2] DAV Univ, Dept Chem, Pathankot Jalandhar Rd, Jalandhar 144001, Punjab, India

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 02期

关键词：

QUINONE METHIDE DERIVATIVES; VINYLOGOUS MICHAEL ADDITION; CONJUGATE ADDITION; 1,6-CONJUGATE ADDITION; BETA-KETOESTERS; 4+2 CYCLIZATION; CASCADE; CONSTRUCTION; CATALYSIS; REMOTE;

D O I：

10.1039/d1qo01561c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Due to their unique activation modes, small organic molecule catalysts (organocatalysts) have proved their potential in facilitating the remote functionalizations of unsaturated acceptors with extended conjugation. The organocatalytic 1,6-addition reaction involving the attack of nucleophiles on the delta-carbon of the alpha,beta,gamma,delta-unsaturated acceptors has emerged as an excellent strategy to create a stereocenter at the delta-site with high regio- and stereo-control. Organocatalysis has also opened the window for developing complex domino reactions involving the 1,6-addition step. Tremendous advancement has been accomplished in the organocatalytic asymmetric 1,6-addition and related domino reactions for the stereocontrolled synthesis of complex molecular structures bearing multiple stereocenters. This review article summarizes the significant advancement in stereoselective domino reactions involving 1,6-addition as a critical step.

引用

页码：572 / 592

页数：21

共 89 条

[1]

Adamo MFA, 2007, HETEROCYCLES, V71, P1173

[2] Multicomponent synthesis of spiroisoxazolines [J].

Adamo, MFA ;

Donati, D ;

Duffy, EF ;

Sarti-Fantoni, P .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8395-8399

[3] 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

[4] Catalytic Asymmetric Conjugate Addition of Nitroalkanes to 4-Nitro-5-styrylisoxazoles [J].

Baschieri, Andrea ;

Bernardi, Luca ;

Ricci, Alfredo ;

Suresh, Surisetti ;

Adamo, Mauro F. A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9342-9345

[5] Organocatalytic asymmetric 1,6-additions of β-ketoesters and glycine imine [J].

Bernardi, Luca ;

Lopez-Cantarero, Jesus ;

Niess, Barbara ;

Jlrgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5772-5778

[6] Organocatalytic Asymmetric 1,6-Addition Reactions [J].

Biju, Akkattu T. .

CHEMCATCHEM, 2011, 3 (12) :1847-1849

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

Bui, T ;

Barbas, CF .

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

[8] Synthesis of Cyclopropane Spirooxindoles by means of a Vinylogous Organocatalytic Cascade [J].

Cesar da Silva, Rodrigo ;

Chatterjee, Indranil ;

Escudero-Adan, Eduardo ;

Weber Paixao, Marcio ;

Melchiorre, Paolo .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (04) :466-469

[9] Recent Progress in Organocatalytic Asymmetric Domino Transformations [J].

Chanda, Tanmoy ;

Zhao, John C. -G. .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (01) :2-79

[10] Vinylogous Organocatalytic Triple Cascade Reaction: Forging Six Stereocenters in Complex Spiro-Oxindolic Cyclohexanes [J].

Chatterjee, Indranil ;

Bastida, David ;

Melchiorre, Paolo .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (16) :3124-3130

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