Asymmetric Synthesis of Highly Substituted β-Lactones through Oxidative Carbene Catalysis with LiCl as Cooperative Lewis Acid

被引：131

作者：

Bera, Srikrishna ^{[1
]}

Samanta, Ramesh C. ^{[1
]}

Daniliuc, Constantin G. ^{[1
]}

Studer, Armido ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 36期

关键词：

asymmetric synthesis; cooperative catalysis; beta-lactones; N-heterocyclic carbenes; organo catalysis; N-HETEROCYCLIC CARBENES; NHC CATALYSIS; STEREOSELECTIVE-SYNTHESIS; DOMINO REACTIONS; ACYL AZOLIUMS; ALDEHYDES; ORGANOCATALYSIS; INHIBITOR; ENALS; DESYMMETRIZATION;

D O I：

10.1002/anie.201405200

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of enals with beta-diketones, beta-ketoesters, and malonates bearing a beta-oxyalkyl substituent at the alpha-position by oxidative NHC catalysis to provide highly substituted beta-lactones is described. Reactions occur with excellent diastereo- and enantioselectivity. The organo cascade comprises two C-C bond formations and one C-O bond formation. Up to four contiguous stereogenic centers including two fully substituted stereocenters are formed in the cascade.

引用

页码：9622 / 9626

页数：5

共 55 条

[1]

[Anonymous], ANGEW CHEM

[2] Enantioselective cyclopropanation of enals by oxidative N-heterocyclic carbene catalysis [J].

Biswas, Anup ;

De Sarkar, Suman ;

Tebben, Ludger ;

Studer, Armido .

CHEMICAL COMMUNICATIONS, 2012, 48 (42) :5190-5192

[3] Highly Stereoselective Synthesis of 1,2,3-Trisubstituted Indanes via Oxidative N-Heterocyclic Carbene-Catalyzed Cascades [J].

Biswas, Anup ;

De Sarkar, Suman ;

Froehlich, Roland ;

Studer, Armido .

ORGANIC LETTERS, 2011, 13 (18) :4966-4969

[4] β-Lactams and β-lactones as activity-based probes in chemical biology [J].

Boettcher, Thomas ;

Sieber, Stephan A. .

MEDCHEMCOMM, 2012, 3 (04) :408-417

[5] Organocatalytic umpolung: N-heterocyclic carbenes and beyond [J].

Bugaut, Xavier ;

Glorius, Frank .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3511-3522

[6] N-Heterocyclic Carbene-Catalyzed Ireland-Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones [J].

Candish, Lisa ;

Lupton, David W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (01) :58-61

[7] Enantioselective, cyclopentene-forming annulations via NHC-catalyzed benzoin-oxy-cope reactions [J].

Chiang, Pei-Chen ;

Kaeobamrung, Juthanat ;

Bode, Jeffrey W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (12) :3520-+

[8]

Cohen D. T., 2012, ANGEW CHEM, V124, P7421, DOI 10.1002/ange.201203382

[9] Catalytic Dynamic Kinetic Resolutions with N-Heterocyclic Carbenes: Asymmetric Synthesis of Highly Substituted β-Lactones [J].

Cohen, Daniel T. ;

Eichman, Chad C. ;

Phillips, Eric M. ;

Zarefsky, Emily R. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (29) :7309-7313

[10] Cooperative Lewis acid/N-heterocyclic carbene catalysis [J].

Cohen, Daniel T. ;

Scheidt, Karl A. .

CHEMICAL SCIENCE, 2012, 3 (01) :53-57

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