Asymmetric Nazarov Reaction Catalyzed by Chiral Tris(oxazoline)/Copper(II)

被引:105
作者
Cao, Peng [1 ]
Deng, Chao [1 ]
Zhou, You-Yun [1 ]
Sun, Xiu-Li [1 ]
Zheng, Jun-Cheng [1 ]
Xie, Zuowei [2 ]
Tang, Yong [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[2] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China
关键词
asymmetric catalysis; copper; cyclization; diastereoselectivity; Nazarov cyclization; MICHAEL ADDITION; ENANTIOSELECTIVE HYDROGENATION; STEREOSELECTIVE-SYNTHESIS; EFFICIENT CATALYSIS; THREEFOLD SYMMETRY; CYCLIZATION; COMPLEXES; LIGANDS; (+/-)-MERRILACTONE-A; REARRANGEMENT;
D O I
10.1002/anie.200907266
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Beverly Hills copper(II): A highly efficient catalytic asymmetric Nazarov reaction has been developed through control of the enantioselectivity of the cyclization step, affording chiral O-heterohexahydroinde-nones in excellent yields with excellent enantioselectivity and diastereoselectivity. HFIP = hexafluoro-2-propanol, BArF = tetrakis[3,5-bis(trifluoromethyl)phenyl] borate. © 2010 Wlley-VCH Verlag GmbH &. Co. KGaA, Weinheim.
引用
收藏
页码:4463 / 4466
页数:4
相关论文
共 65 条
[1]   Catalytic asymmetric nazarov reactions promoted by chiral Lewis acid complexes [J].
Aggarwal, VK ;
Beffield, AJ .
ORGANIC LETTERS, 2003, 5 (26) :5075-5078
[2]   Traceless Chiral Auxiliaries for the Allene Ether Nazarov Cyclization [J].
Banaag, April R. ;
Tius, Marcus A. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8133-8141
[3]   Design of chiral auxiliaries for the allene ether Nazarov cyclization [J].
Banaag, April R. ;
Tius, Marcus A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5328-+
[4]   Interrupting the nazarov cyclization with indoles [J].
Basak, Ashok K. ;
Tius, Marcus A. .
ORGANIC LETTERS, 2008, 10 (18) :4073-4076
[5]   Total synthesis of (±)-terpestacin and (±)-11-epi-terpestacin [J].
Berger, Gideon O. ;
Tius, Marcus A. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17) :6473-6480
[6]   Formal Synthesis of (±)-Roseophilin [J].
Bitar, Abdallah Y. ;
Frontier, Alison J. .
ORGANIC LETTERS, 2009, 11 (01) :49-52
[7]   Multistep One-Pot, Wittig/Nazarov Reaction for Construction of Cyclopentenone with Diazo Compounds and Acid Chlorides [J].
Cao, Peng ;
Sun, Xiu-Li ;
Zhu, Ben-Hu ;
Shen, Qi ;
Xie, Zuowei ;
Tang, Yong .
ORGANIC LETTERS, 2009, 11 (14) :3048-3051
[8]  
CORDIER P, 2009, ANGEW CHEM, V121, P8913
[9]   Silver and Bronsted Acid Catalyzed Nazarov-Type Cyclizations To Generate Benzofulvenes [J].
Cordier, Pierre ;
Aubert, Corinne ;
Malacria, Max ;
Lacote, Emmanuel ;
Gandon, Vincent .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (46) :8757-8760
[10]   SILICON-DIRECTED NAZAROV CYCLIZATION [J].
DENMARK, SE ;
JONES, TK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (09) :2642-2645