Synergistic Catalysis: Asymmetric Synthesis of Cyclopentanes Bearing Four Stereogenic Centers

被引：16

作者：

Zhang, Kaiheng ^{[1
]}

Meazza, Marta ^{[1
]}

Izaga, Anabel ^{[1
,2
]}

Contamine, Clotilde ^{[1
,3
]}

Concepcion Gimeno, M. ^{[2
]}

Herrera, Raquel P. ^{[4
]}

Rios, Ramon ^{[1
]}

机构：

[1] Univ Southampton, Sch Chem, Highfield Campus, Southampton SO17 1BJ, Hants, England

[2] Univ Zaragoza, CSIC, Dept Quim Organ, ISQCH, E-50009 Zaragoza, Spain

[3] Ensicaen, 6 Blvd Marechal Juin,CS 45053, F-14050 Caen, France

[4] Univ Zaragoza, Dept Quim Organ, CSIC, Lab Organocatalisis Asimetr,ISQCH, E-50009 Zaragoza, Spain

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

synergistic catalysis; organocatalysis; cyclopentanes; asymmetric synthesis; cycloaddition; ORGANOCATALYTIC DOMINO REACTIONS; VINYL CYCLOPROPANES; ALPHA-ALLYLATION; ALDEHYDES; ENALS; STRATEGY;

D O I：

10.1055/s-0036-1588347

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present a formal [3+2] cycloaddition based on synergistic catalysis. Vinylcyclopropanes derived from cyanoesters react with enals by dual activation using palladium(0) and secondary amines to form the corresponding cyclopentanes in good yields and stereoselectivities.

引用

页码：167 / 174

页数：8

共 26 条

[1] Organocatalytic Domino Reactions
Alba, Andrea-Nekane
Companyo, Xavier
Viciano, Monica
Rios, Ramon
[J]. CURRENT ORGANIC CHEMISTRY, 2009, 13 (14) : 1432 - 1474
[2] Synergistic catalysis: A powerful synthetic strategy for new reaction development
Allen, Anna E.
MacMillan, David W. C.
[J]. CHEMICAL SCIENCE, 2012, 3 (03) : 633 - 658
[3] Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita-Baylis-Hillman carbonates
Ceban, Victor
Putaj, Piotr
Meazza, Marta
Pitak, Mateusz B.
Coles, Simon J.
Vesely, Jan
Rios, Ramon
[J]. CHEMICAL COMMUNICATIONS, 2014, 50 (56) : 7447 - 7450
[4] Asymmetric Organocatalytic Benzylation of α,β-Unsaturated Aldehydes with Toluenes
Dell'Amico, Luca
Companyo, Xavier
Naicker, Tricia
Brauer, Thomas M.
Jorgensen, Karl Anker
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) : 5262 - 5265
[5] Enders D., 2007, Angew. Chem, V119, P1590, DOI DOI 10.1002/ange.200603129
[6] Asymmetric organocatalytic domino reactions
Enders, Dieter
Grondal, Christoph
Huettl, Matthias R. M.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) : 1570 - 1581
[7] Asymmetric [3+2] Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Aldehydes by Synergistic Palladium and Organocatalysis
Halskov, Kim Soholm
Naesborg, Line
Tur, Fernando
Jorgensen, Karl Anker
[J]. ORGANIC LETTERS, 2016, 18 (09) : 2220 - 2223
[8] Palladium/Chiral Amine Co-catalyzed Enantioselective β-Arylation of α,β-Unsaturated Aldehydes
Ibrahem, Ismail
Ma, Guangning
Afewerki, Samson
Cordova, Armando
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (03) : 878 - 882
[9] One-Pot Three-Component Catalytic Enantioselective Synthesis of Homoallylboronates
Ibrahem, Ismail
Breistein, Palle
Cordova, Armando
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) : 12036 - 12041
[10] Enantioselective Conjugate Silyl Additions to α,β-Unsaturated Aldehydes Catalyzed by Combination of Transition Metal and Chiral Amine Catalysts
Ibrahem, Ismail
Santoro, Stefano
Himo, Fahmi
Cordova, Armando
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) : 245 - 252

← 1 2 3 →