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 50 条

[1] Enantioselective Synthesis of Substituted δ-Lactones by Cooperative Oxidative N-Heterocyclic Carbene and Lewis Acid Catalysis
Bera, Srikrishna
Daniliuc, Constantin G.
Studer, Armido
ORGANIC LETTERS, 2015, 17 (20) : 4940 - 4943
[2] Cooperative Lewis acid/N-heterocyclic carbene catalysis
Cohen, Daniel T.
Scheidt, Karl A.
CHEMICAL SCIENCE, 2012, 3 (01) : 53 - 57
[3] Asymmetric Synthesis of Spiro-oxindole-ε-lactones through N-Heterocyclic Carbene Catalysis
Liu, Qang
Li, Sun
Chen, Xiang-Yu
Rissanen, Kari
Enders, Dieter
ORGANIC LETTERS, 2018, 20 (12) : 3622 - 3626
[4] Access to Amide from Aldimine via Aerobic Oxidative Carbene Catalysis and LiCI as Cooperative Lewis Acid
Wang, Guanjie
Fu, Zhenqian
Huang, Wei
ORGANIC LETTERS, 2017, 19 (13) : 3362 - 3365
[5] Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates
Cardinal-David, Benoit
Raup, Dustin E. A.
Scheidt, Karl A.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) : 5345 - +
[6] Tertiary amine-Lewis acid cooperative asymmetric catalysis
Dixon, Darren J.
Sladojevich, Filippo
Yang, Ting
Ferrali, Alessandro
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[7] Bifunctional asymmetric catalysis: Cooperative lewis acid/base systems
Paull, Daniel H.
Abraham, Ciby J.
Scerba, Michael T.
Alden-Danforth, Ethan
Lectka, Thomas
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (05) : 655 - 663
[8] Contact ion pair directed Lewis acid catalysis:: Asymmetric synthesis of trans-configured β-lactones
Kull, Thomas
Peters, Rene
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (29) : 5461 - 5464
[9] Catalytic Asymmetric Synthesis of trans-Configured β-Lactones: Cooperation of Lewis Acid and Ion Pair Catalysis
Kull, Thomas
Cabrera, Jose
Peters, Rene
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) : 9132 - 9139
[10] N-Heterocyclic Carbene and Bronsted Acid Cooperative Catalysis: Asymmetric Synthesis of trans-γ-Lactams
Zhao, Xiaodan
DiRocco, Daniel A.
Rovis, Tomislav
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) : 12466 - 12469

← 1 2 3 4 5 →