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
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 05期
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
[31]   Asymmetric reductive ring-opening of bicyclic olefins catalyzed by palladium and nickel complexes [J].
Li, LP ;
Rayabarapu, DK ;
Nandi, M ;
Cheng, CH .
ORGANIC LETTERS, 2003, 5 (10) :1621-1624
[32]   Palladium-catalyzed enantioselective ring opening of oxabicyclic alkenes with organozinc halides [J].
Li, M ;
Yan, XX ;
Hong, W ;
Zhu, XZ ;
Cao, BX ;
Sun, J ;
Hou, XL .
ORGANIC LETTERS, 2004, 6 (16) :2833-2835
[33]   Nickel-catalyzed synthesis of benzocoumarins: Application to the total synthesis of arnottin I [J].
Madan, Sachin ;
Cheng, Chien-Hong .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) :8312-8315
[34]   Copper-Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Grignard and Aluminum Reagents [J].
Millet, Renaud ;
Gremaud, Ludovic ;
Bernardez, Tania ;
Palais, Laetitia ;
Alexakis, Alexandre .
SYNTHESIS-STUTTGART, 2009, (12) :2101-2112
[35]   Rh(I)-Catalyzed Ring-Opening of Hetaryne-furan Diels-Alder Adducts: Rapid Access to Stereochemically Defined Heterocyclic Scaffolds [J].
Nguyen, Trung D. ;
Webster, Robert ;
Lautens, Mark .
ORGANIC LETTERS, 2011, 13 (06) :1370-1373
[36]   Rhodium-catalyzed asymmetric cyclodimerization of oxa- and azabicyclic alkenes [J].
Nishimura, Takahiro ;
Kawamoto, Takahiro ;
Sasaki, Keigo ;
Tsurumaki, Eiji ;
Hayashi, Tamio .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) :1492-+
[37]   Pallladium-catalyzed multistep reactions involving ring closure of 2-iodophenoxyallenes and ring opening of bicyclic alkenes [J].
Parthasarathy, K ;
Jeganmohan, M ;
Cheng, CH .
ORGANIC LETTERS, 2006, 8 (04) :621-623
[38]   Cu(OTF)2-Catalyzed Isomerization of 7-Oxabicyclic Alkenes: A Practical Route to the Synthesis of 1-Naphthol Derivatives; [J].
Peng, Fangzhi ;
Fan, Baomin ;
Shao, Zhihui ;
Pu, Xuewei ;
Li, Penghui ;
Zhang, Hongbin .
SYNTHESIS-STUTTGART, 2008, (19) :3043-3046
[39]   Cyclization of oxa-bicyclic alkenes with β-iodo-(Z)-propenoates and o-iodobenzoate catalyzed by nickel complexes:: A simple efficient route to annulated coumarins [J].
Rayabarapu, DK ;
Shukla, P ;
Cheng, CH .
ORGANIC LETTERS, 2003, 5 (25) :4903-4906
[40]   Regio- and stereoselective reductive coupling of bicyclic alkenes with propiolates catalyzed by nickel complexes:: A novel route to functionalized 1,2-dihydroarenes and γ-lactones [J].
Rayabarapu, DK ;
Cheng, CH .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (13) :3164-3169
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