Geminal bis(silane)-controlled regio- and stereoselective oxidative Heck reaction of enol ethers with terminal alkenes to give push-pull 1,3-dienes

被引:16
作者
Li, Linjie [1 ]
Chu, Yang [1 ]
Gao, Lu [1 ]
Song, Zhenlei [1 ,2 ]
机构
[1] Sichuan Univ, West China Sch Pharm, Educ Minist, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu 610041, Peoples R China
[2] Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Chengdu 610041, Peoples R China
关键词
H BOND ACTIVATION; CROSS-COUPLING REACTION; SELECTIVE ACCESS; C-C; FUNCTIONALIZATION; ACRYLATES; EFFICIENT; ARYL; OLEFINATION; REARRANGEMENT;
D O I
10.1039/c5cc06448a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A geminal bis(silane)-controlled regio- and stereoselective oxidative Heck reaction of enol ethers with terminal alkenes has been developed. The reaction proceeds with alpha,beta-coupling regioselectivity to give push-pull Z,E-1,3-dienes in good yields. The product showed valuable utility in Sakurai homoallylation with acetals to generate alpha-substituted-gamma-keto esters with good anti-selectivity.
引用
收藏
页码:15546 / 15549
页数:4
相关论文
共 74 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[3]   Palladium-Catalyzed Dehydrogenative Coupling of Furans with Styrenes [J].
Aouf, Chahinez ;
Thiery, Emilie ;
Le Bras, Jean ;
Muzart, Jacques .
ORGANIC LETTERS, 2009, 11 (18) :4096-4099
[4]   C-H Bond Activation by f-Block Complexes [J].
Arnold, Polly L. ;
McMullon, Max W. ;
Rieb, Julia ;
Kuehn, Fritz E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (01) :82-100
[5]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
[6]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365
[7]  
Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
[8]   RhIII-Catalyzed Oxidative Olefination of Vinylic C-H Bonds: Efficient and Selective Access to Di-unsaturated α-Amino Acid Derivatives and Other Linear 1,3-Butadienes [J].
Besset, Tatiana ;
Kuhl, Nadine ;
Patureau, Frederic W. ;
Glorius, Frank .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (26) :7167-7171
[9]   Using Rh(III)-Catalyzed C-H Activation as a Tool for the Selective Functionalization of Ketone-Containing Molecules [J].
Boultadakis-Arapinis, Melissa ;
Hopkinson, Matthew N. ;
Glorius, Frank .
ORGANIC LETTERS, 2014, 16 (06) :1630-1633
[10]   ENZYME CATALYSIS C-H activation is a Reiske business [J].
Bruner, Steven D. .
NATURE CHEMISTRY, 2011, 3 (05) :342-343