Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Oxa(Aza)bicyclic Alkenes with Carbanion Nucleophiles

被引:8
作者
Wu, Ruihua [1 ]
Yang, Wen [1 ]
Cheng, Guo [1 ]
Li, Yue [1 ]
Yang, Dingqiao [1 ]
机构
[1] South China Normal Univ, Key Lab Theoret Chem Environm, Minist Educ, Sch Chem & Environm, Guangzhou 510006, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
transition metal catalyst; oxa(aza)bicyclic alkene; carbanion nucleophile; asymmetric ring-opening; OXABICYCLIC ALKENES; AZABICYCLIC ALKENES; HETEROBICYCLIC ALKENES; BORONIC ACIDS; GRIGNARD; OXABENZONORBORNADIENES; ARYL; REAGENTS; ALKYNES; FUNCTIONALIZATION;
D O I
10.6023/cjoc201604006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The recent progress in transition metal-catalyzed asymmetric ring-opening reactions of oxa(aza)bicyclic alkenes with carbanion nucleophiles is reviewed with focus on the influence of the types of transition metal catalysts, carbanion nucleophiles, ligands, the structures of oxa(aza)bicyclic alkenes, solvents and additives on the asymmetric ring-opening reactions. Moreover, the parties of possible mechanisms for the asymmetric ring-opening reactions are also discussed.
引用
收藏
页码:2368 / 2379
页数:12
相关论文
共 63 条
[1]   Iridium-catalyzed asymmetric allylic substitution with aryl zinc reagents [J].
Alexakis, Alexandre ;
El Hajjaji, Samir ;
Polet, Damien ;
Rathgeb, Xavier .
ORGANIC LETTERS, 2007, 9 (17) :3393-3395
[2]   Copper-catalyzed ring-opening of heterobicyclic alkenes with Grignard reagents:: Remarkably high anti-stereocontrol [J].
Arrayás, RG ;
Cabrera, S ;
Carretero, JC .
SYNTHESIS-STUTTGART, 2006, (07) :1205-1219
[3]   Copper-catalyzed anti-stereocontrolled ring-opening of azabicyclic alkenes with grignard reagents [J].
Arrayás, RG ;
Cabrera, S ;
Carretero, JC .
ORGANIC LETTERS, 2005, 7 (02) :219-221
[4]   Copper-catalyzed anti-stereocontrolled ring opening of oxabicyclic alkenes with Grignard reagents [J].
Arrayás, RG ;
Cabrera, S ;
Carretero, JC .
ORGANIC LETTERS, 2003, 5 (08) :1333-1336
[5]   Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with organolithium reagents [J].
Bos, Pieter H. ;
Rudolph, Alena ;
Perez, Manuel ;
Fananas-Mastral, Martin ;
Harutyunyan, Syuzanna R. ;
Feringa, Ben L. .
CHEMICAL COMMUNICATIONS, 2012, 48 (12) :1748-1750
[6]   Fesulphos-palladium(II) complexes as well-defined catalysts for enantioselective ring opening of meso heterobicyclic alkenes with organozinc reagents [J].
Cabrera, S ;
Arrayás, RG ;
Alonso, I ;
Carretero, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17938-17947
[7]   Pd-catalyzed ring opening of oxa- and azabicyclic alkenes with aryl and vinyl halides: Efficient entry to 2-substituted 1,2-dihydro-1-naphthols and 2-substituted 1-naphthols [J].
Chen, Chi-Li ;
Martin, Stephen F. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13) :4810-4817
[8]   Palladium-Catalyzed Ring-Opening Reaction of Oxa/Azabenzonorbornadienes with Aryl Acetylenes [J].
Chen Hualei ;
Li Sifeng ;
Xu Jianbin ;
Yang Qingjing ;
Liu Shanshan ;
Zhou Yongyun ;
Huang Chao ;
Fan Baomin .
ACTA CHIMICA SINICA, 2013, 71 (09) :1243-1247
[9]   Palladium/Silver-Cocatalyzed Tandem Reactions of Oxabenzonorbornadienes with Substituted Arylacetylenes: A Simple Method for the Preparation of 1,2-Diarylethanones and 1,2-Diary Diarylacetylenes [J].
Chen, Jingchao ;
Liu, Shanshan ;
Zhou, Yongyun ;
Li, Sifeng ;
Lin, Chengyuan ;
Bian, Zhaoxiang ;
Fan, Baomin .
ORGANOMETALLICS, 2015, 34 (17) :4318-4322
[10]   Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Azabicyclic Alkenes [J].
Cheng, Hanchao ;
Liang, Xiuli ;
Li, Xiaolu ;
Long, Yuhua ;
Yang, Dingqiao .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (03) :433-443