Chiral Lewis acid-catalyzed enantioselective cyclopropanation and C-H insertion reactions of vinyl ketones with α-diazoesters

被引：22

作者：

Zhao, Peng ^{[1
]}

Wu, Simeng ^{[1
]}

Ke, Chaoqi ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 70期

基金：

中国国家自然科学基金;

关键词：

DIAZOCARBONYL COMPOUNDS; SUBSTITUTED ACROLEINS; ASYMMETRIC REACTIONS; EFFICIENT SYNTHESIS; CARBONYL-COMPOUNDS; LIGANDS; BOND; FUNCTIONALIZATION; CYCLOADDITIONS; ALDEHYDES;

D O I：

10.1039/c8cc05420g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective cyclopropanation and C-H insertion reactions of alpha-substituted vinyl ketones with alpha-diazoesters have been accomplished using a N,N'-dioxide-scandium(III) complex catalyst. Various tetrasubstituted cyclopropanes and E-enone derivatives bearing a chiral ester substituent were obtained simultaneously with good yields and excellent enantioselectivities.

引用

页码：9837 / 9840

页数：4

共 37 条

[1] Acid catalyzed reactions of α,β-unsaturated aldehydes and ethyl diazoacetate [J].

Branstetter, B ;

Hossain, MM .

TETRAHEDRON LETTERS, 2006, 47 (02) :221-223

[2] Efficient Synthesis of 1,2,3-Triazoles by Copper-Mediated C-N and N-N Bond Formation Starting From N-Tosylhydrazones and Amines [J].

Chen, Zhengkai ;

Yan, Qiangqiang ;

Yi, Hong ;

Liu, Zhanxiang ;

Lei, Aiwen ;

Zhang, Yuhong .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (42) :13692-13697

[3] Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].

Davies, Huw M. L. ;

Manning, James R. .

NATURE, 2008, 451 (7177) :417-424

[4] Guiding principles for site selective and stereoselective intermolecular C-H functionalization by donor/acceptor rhodium carbenes [J].

Davies, Huw M. L. ;

Morton, Daniel .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1857-1869

[5] Application of donor/acceptor-carbenoids to the synthesis of natural products [J].

Davies, Huw M. L. ;

Denton, Justin R. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3061-3071

[6] Rh-Catalyzed Intermolecular Reactions of α-Alkyl-α-Diazo Carbonyl Compounds with Selectivity over β-Hydride Migration [J].

DeAngelis, Andrew ;

Panish, Robert ;

Fox, Joseph M. .

ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (01) :115-127

[7]

DOYLE MP, 1979, TETRAHEDRON LETT, P4429

[8] Oxazaborolidinium Ion-Catalyzed Cyclopropanation of α-Substituted Acroleins: Enantioselective Synthesis of Cyclopropanes Bearing Two Chiral Quaternary Centers [J].

Gao, Lizhu ;

Hwang, Geum-Sook ;

Ryu, Do Hyun .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (51) :20708-20711

[9] Catalytic enantioselective 1,3-dipolar cycloadditions of alkyl diazoacetates with α,β-disubstituted acroleins [J].

Gao, Lizhu ;

Hwang, Geum-Sook ;

Lee, Mi Young ;

Ryu, Do Hyun .

CHEMICAL COMMUNICATIONS, 2009, (36) :5460-5462

[10] Construction of stereodefined 1,1,2,2-tetrasubstituted cyclopropanes by acid catalyzed reaction of aryldiazoacetates and α-substituted acroleins [J].

Hashimoto, Takuya ;

Naganawa, Yuki ;

Kano, Taichi ;

Maruoka, Keiji .

CHEMICAL COMMUNICATIONS, 2007, (48) :5143-5145

← 1 2 3 4 →