Pd(0)-Catalysed asymmetric reductive Heck-type cyclization of (Z)-1-iodo-1,6-dienes and enantioselective synthesis of quaternary tetrahydropyridines

被引：26
作者：
Hou, Longlei [1 ,2 ]
Yuan, Yuejie [1 ,2 ]
Tong, Xiaofeng [1 ,2 ,3 ]
机构：
[1] East China Univ Sci & Technol, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China
[3] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 22期
基金：
中国国家自然科学基金;
关键词：
CATALYZED TRANSFER HYDROGENATION; VINYLIC SUBSTITUTION; CONJUGATE ADDITION; ARYL HALIDES; WATER; CONSTRUCTION; ALKALOIDS; HETEROCYCLES; PIPERIDINES; LIGANDS;
D O I：
10.1039/c7ob00762k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Pd(0)/(S)-p-MeO-BnPHOX catalytic system has been established for the asymmetric reductive Heck reaction of (Z)-1-iodo-1,6-dienes, which affords quaternary tetrahydropyridines with good to excellent enantioselectivities. This reaction tolerates a wide range of substituted alkene moieties, including 1,1-disubstituted, 1,1,2-trisubstituted as well as 1,2-disubstituted alkenes.
引用
收藏
页码：4803 / 4806
页数：4
相关论文
共 40 条
[1]   CONJUGATE ADDITION VS VINYLIC SUBSTITUTION IN PALLADIUM-CATALYZED REACTION OF ARYL HALIDES WITH BETA-SUBSTITUTED-ALPHA,BETA-ENONES AND BETA-SUBSTITUTED-ALPHA,BETA-ENALS [J].
AMORESE, A ;
ARCADI, A ;
BERNOCCHI, E ;
CACCHI, S ;
CERRINI, S ;
FEDELI, W ;
ORTAR, G .
TETRAHEDRON, 1989, 45 (03) :813-828
[2]   The palladium-catalysed vinylic substitution of vinyl triflates with beta-substituted-alpha,beta-unsaturated carbonyl compounds. An application to the synthesis of cardenolides. [J].
Arcadi, A ;
Cacchi, S ;
Fabrizi, G ;
Marinelli, F ;
Pace, P .
TETRAHEDRON, 1996, 52 (20) :6983-6996
[3]   Investigation of the Electronic Origin of Asymmetric Induction in Palladium-Catalyzed Allylic Substitutions with Phosphinooxazoline (PHOX) Ligands by Hammett and Swain-Lupton Analysis of the 13C NMR Chemical Shifts of the (π-Allyl)palladium Intermediates [J].
Armstrong, Paul B. ;
Dembicer, Elizabeth A. ;
DesBois, Andrew J. ;
Fitzgerald, Jay T. ;
Gehrmann, Janet K. ;
Nelson, Nathaniel C. ;
Noble, Amelia L. ;
Bunt, Richard C. .
ORGANOMETALLICS, 2012, 31 (19) :6933-6946
[4]  
Behenna DC, 2012, NAT CHEM, V4, P130, DOI [10.1038/nchem.1222, 10.1038/NCHEM.1222]
[5]   Synthesis of piperidines [J].
Buffat, MGP .
TETRAHEDRON, 2004, 60 (08) :1701-1729
[6]   PALLADIUM-CATALYZED CONJUGATE ADDITION TYPE REACTION OF ARYL IODIDES WITH ALPHA,BETA-UNSATURATED KETONES [J].
CACCHI, S ;
ARCADI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4236-4240
[7]   THE PALLADIUM-CATALYZED HYDROARYLATION AND HYDROVINYLATION OF CARBON CARBON MULTIPLE BONDS - NEW PERSPECTIVES IN ORGANIC-SYNTHESIS [J].
CACCHI, S .
PURE AND APPLIED CHEMISTRY, 1990, 62 (04) :713-722
[8]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[9]  
2-V
[10]   Tetrahydroxydiboron-Mediated Palladium-Catalyzed Transfer Hydrogenation and Deuteriation of Alkenes and Alkynes Using Water as the Stoichiometric H or D Atom Donor [J].
Cummings, Steven P. ;
Thanh-Ngoc Le ;
Fernandez, Gilberto E. ;
Quiambao, Lorenzo G. ;
Stokes, Benjamin J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (19) :6107-6110
1234