Rhodium-Catalyzed Asymmetric Conjugate Alkynylation of β,γ-Unsaturated α-Ketoesters

被引：34

作者：

Zhi, Yanle ^{[1
]}

Huang, Jianhang ^{[1
]}

Liu, Na ^{[1
]}

Lu, Tao ^{[1
,2
]}

Dou, Xiaowei ^{[1
]}

机构：

[1] China Pharmaceut Univ, Dept Organ Chem, 24 Tongjiaxiang, Nanjing 210009, Jiangsu, Peoples R China

[2] China Pharmaceut Univ, State Key Lab Nat Med, 24 Tongjiaxiang, Nanjing 210009, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 09期

基金：

中国国家自然科学基金;

关键词：

C-H BONDS; BINARY-ACID CATALYSIS; TERMINAL ALKYNES; CARBONYL-COMPOUNDS; ENANTIOSELECTIVE HYDROALKYNYLATION; ENONES; SILYLACETYLENES; LIGANDS; KETONES; AZABENZONORBORNADIENES;

D O I：

10.1021/acs.orglett.7b00909

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of catalytic asymmetric conjugate alkynylation of beta,gamma-unsaturated alpha-ketoesters is reported. By using Rh(I)/(R)-DM-binap complex as the catalyst and diphenyl[(triisopropylsilyl)ethynyl]methanol as the alkynylating reagent, the alkynylation reaction proceeded smoothly to afford alpha-ketoesters bearing a propargylic chiral center at gamma position in good yields with high enantioselectivities.

引用

页码：2378 / 2381

页数：4

共 57 条

[1] Iridium-Catalyzed Enantioselective Hydroalkynylation of Enamides for the Synthesis of Homopropargyl Amides [J].

Bai, Xiao-Yan ;

Wang, Zi-Xuan ;

Li, Bi-Jie .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (31) :9007-9011

[2] Enantioselective Zinc-Mediated Conjugate Addition of Terminal Alkynes to Enones [J].

Blay, Gonzalo ;

Cardona, Luz ;

Pedro, Jose R. ;

Sanz-Marco, Amparo .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (41) :12966-12969

[3]

Cordova A., 2010, Catalytic Asymmetric Conjugate Reactions

[4] Rhodium-catalyzed enantioselective desymmetrization of bicyclic hydrazines with alkynylboronic esters [J].

Crotti, Stefano ;

Bertolini, Ferruccio ;

Macchia, Franco ;

Pineschi, Mauro .

CHEMICAL COMMUNICATIONS, 2008, (27) :3127-3129

[5] Practical Asymmetric Conjugate Alkynylation of Meldrum's Acid-Derived Acceptors: Access to Chiral β-Alkynyl Acids [J].

Cui, Sheng ;

Walker, Shawn D. ;

Woo, Jacqueline C. S. ;

Borths, Christopher J. ;

Mukherjee, Herschel ;

Chen, Maosheng J. ;

Faul, Margaret M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (02) :436-+

[6] Substituted (E)-2-Oxo-3-butenoates: Reagents for Every Enantioselectively-Catalyzed Reaction [J].

Desimoni, Giovanni ;

Faita, Giuseppe ;

Quadrelli, Paolo .

CHEMICAL REVIEWS, 2013, 113 (08) :5924-5988

[7] Asymmetric Conjugate Alkynylation of Cyclic ,-Unsaturated Carbonyl Compounds with a Chiral Diene Rhodium Catalyst [J].

Dou, Xiaowei ;

Huang, Yinhua ;

Hayashi, Tamio .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (03) :1133-1137

[8] Asymmetric Hydroalkynylation of Norbornadienes Promoted by Chiral Iridium Catalysts [J].

Fan, Bao-Min ;

Yang, Qing-jing ;

Hu, Jun ;

Fan, Cai-ling ;

Li, Si-feng ;

Yu, Lu ;

Huang, Chao ;

Tsang, Wing Wai ;

Kwong, Fuk Yee .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (31) :7821-7824

[9] Rh-Catalyzed Highly Enantioselective Hydroalkynylation Reaction of Norbornadiene Derivatives [J].

Fan, Baomin ;

Xu, Jianbin ;

Yang, Qingjing ;

Li, Sifeng ;

Chen, Hualei ;

Liu, Shanshan ;

Yu, Lu ;

Zhou, Yongyun ;

Wang, Lin .

ORGANIC LETTERS, 2013, 15 (23) :5956-5959

[10] Enantioselective Rhodium-Catalyzed Conjugate Alkynylation of 5-Benzylidene Meldrum's Acids with TMS-acetylene [J].

Fillion, Eric ;

Zorzitto, Alexander K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (41) :14608-+

← 1 2 3 4 5 6 →