Iridium-catalyzed asymmetric hydroalkynylation reactions of oxabenzonorbornadienes

被引:46
作者
Hu, Jun [1 ,2 ]
Yang, Qingjing [1 ,2 ]
Xu, Jianbin [1 ,2 ]
Huang, Chao [1 ,2 ]
Fan, Baomin [1 ,2 ]
Wang, Jun [3 ]
Lin, Chengyuan [3 ]
Bian, Zhaoxiang [3 ,4 ]
Chan, Albert S. C. [4 ]
机构
[1] Yunnan Univ Nationalities, State Ethn Affairs Commiss, Key Lab Chem Ethn Med Resources, Kunming 650500, Peoples R China
[2] Yunnan Univ Nationalities, Minist Educ, Kunming 650500, Peoples R China
[3] Hong Kong Baptist Univ, Sch Chinese Med, Hong Kong, Hong Kong, Peoples R China
[4] Hong Kong Baptist Univ, Inst Creat, Hong Kong, Hong Kong, Peoples R China
基金
中国国家自然科学基金;
关键词
RING-OPENING REACTIONS; BICYCLIC ALKENES; OXABICYCLIC ALKENES; 2+2 CYCLOADDITION; NICKEL-COMPLEXES; AZABICYCLIC ALKENES; TERMINAL ALKYNES; EFFICIENT ROUTE; PALLADIUM; DERIVATIVES;
D O I
10.1039/c2ob26775f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxabenzonorbornadienes were found to be suitable substrates for asymmetric hydroalkynylation reactions. Catalyzed by the complex of [Ir(COD)Cl](2) and (R)-SYNPHOS, oxabenzonorbornadienes and terminal alkynes could react smoothly to give the alkynylated products in moderate to good yields (up to 93% yield) and enantioselectivities (up to 85% ee).
引用
收藏
页码:814 / 820
页数:7
相关论文
共 59 条
[21]   [2+2] DIMERIZATION OF NORBORNADIENE AND ITS DERIVATIVES IN THE PRESENCE OF NICKEL-COMPLEXES AND ZINC METAL [J].
HUANG, DJ ;
CHENG, CH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 490 (1-2) :C1-C7
[22]  
Huang DJ, 2000, CHEM-EUR J, V6, P3706, DOI 10.1002/1521-3765(20001016)6:20<3706::AID-CHEM3706>3.0.CO
[23]  
2-P
[24]   Diastereoselective Carbometalation of Oxa- and Azabicyclic Alkenes under Iron Catalysis [J].
Ito, Shingo ;
Itoh, Takuma ;
Nakamura, Masaharu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) :454-457
[25]   Palladium-catalyzed [2+2+2] cocyclotrimerization of benzynes with bicyclic alkenes: An efficient route to anellated 9,10-dihydrophenanthrene derivatives and polyaromatic compounds [J].
Jayanth, TT ;
Jeganmohan, M ;
Cheng, CH .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) :8445-8450
[26]   Rhodium-catalysed asymmetric ring opening reactions with carboxylate nucleophiles [J].
Lautens, M ;
Fagnou, K .
TETRAHEDRON, 2001, 57 (24) :5067-5072
[27]   Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: Catalyst and substrate studies leading to a mechanistic working model [J].
Lautens, M ;
Fagnou, K .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5455-5460
[28]   Rhodium-catalyzed asymmetric alcoholysis and aminolysis of oxabenzonorbornadiene: A new enantioselective carbon-heteroatom bond forming process [J].
Lautens, M ;
Fagnou, K ;
Rovis, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (23) :5650-5651
[29]   Transition metal-catalyzed enantioselective ring-opening reactions of oxabicyclic alkenes [J].
Lautens, M ;
Fagnou, K ;
Hiebert, S .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (01) :48-58
[30]   Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: Application of halide effects in the development of a general process [J].
Lautens, M ;
Fagnou, K ;
Yang, DQ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (48) :14884-14892