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

被引：130

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
Biswas, Anup
De Sarkar, Suman
Tebben, Ludger
Studer, Armido
[J]. CHEMICAL COMMUNICATIONS, 2012, 48 (42) : 5190 - 5192
[3] Highly Stereoselective Synthesis of 1,2,3-Trisubstituted Indanes via Oxidative N-Heterocyclic Carbene-Catalyzed Cascades
Biswas, Anup
De Sarkar, Suman
Froehlich, Roland
Studer, Armido
[J]. ORGANIC LETTERS, 2011, 13 (18) : 4966 - 4969
[4] β-Lactams and β-lactones as activity-based probes in chemical biology
Boettcher, Thomas
Sieber, Stephan A.
[J]. MEDCHEMCOMM, 2012, 3 (04) : 408 - 417
[5] Organocatalytic umpolung: N-heterocyclic carbenes and beyond
Bugaut, Xavier
Glorius, Frank
[J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3511 - 3522
[6] N-Heterocyclic Carbene-Catalyzed Ireland-Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones
Candish, Lisa
Lupton, David W.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (01) : 58 - 61
[7] Enantioselective, cyclopentene-forming annulations via NHC-catalyzed benzoin-oxy-cope reactions
Chiang, Pei-Chen
Kaeobamrung, Juthanat
Bode, Jeffrey W.
[J]. 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
Cohen, Daniel T.
Eichman, Chad C.
Phillips, Eric M.
Zarefsky, Emily R.
Scheidt, Karl A.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (29) : 7309 - 7313
[10] Cooperative Lewis acid/N-heterocyclic carbene catalysis
Cohen, Daniel T.
Scheidt, Karl A.
[J]. CHEMICAL SCIENCE, 2012, 3 (01) : 53 - 57

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