PtCl2-catalyzed hydrative cyclization of trialkyne functionalities to form bicyclic spiro ketones

被引:55
作者
Chang, Hsu-Kai [1 ]
Datta, Swarup [1 ]
Das, Arindam [1 ]
Odedra, Arjan [1 ]
Liu, Rai-Shung [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
关键词
alkynes; cyclization; homogeneous catalysis; platinum; spiroketones;
D O I
10.1002/anie.200700022
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Triple rounds: A regioselective hydrative cyclization of triynes has been developed to give bicyclic β-hydroxy spiro ketones, which undergo subsequent dehydration to give the β,γ- unsaturated ketones (see scheme). Model reactions suggest that this platinum catalysis includes two selective hydrations, an alkyne insertion, and an aldol condensation. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4744 / 4747
页数:4
相关论文
共 29 条
[11]   Synthesis of triazoles from nonactivated terminal alkynes via the three-component coupling reaction using a Pd(0)-Cu(I) bimetallic catalyst [J].
Kamijo, S ;
Jin, TN ;
Huo, ZB ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) :7786-7787
[12]   Gold(I)-catalyzed conia-ene reaction of β-ketoesters with alkynes [J].
Kennedy-Smith, JJ ;
Staben, ST ;
Toste, FD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) :4526-4527
[13]  
Mizushima E, 2002, ANGEW CHEM INT EDIT, V41, P4563, DOI 10.1002/1521-3773(20021202)41:23<4563::AID-ANIE4563>3.0.CO
[14]  
2-U
[15]  
Mizushima E., 2002, Angew. Chem, V114, P4745, DOI DOI 10.1002/1521-3757(20021202)114:23ANDLT
[16]  
4745::AID-ANGE4745ANDGT
[17]  
3.0.CO
[18]  
2-S
[19]   Ruthenium-catalyzed aromatization of enediynes via highly regioselective nucleophilic additions on a π-alkyne functionality.: A useful method for the synthesis of functionalized benzene derivatives [J].
Odedra, A ;
Wu, CJ ;
Pratap, TB ;
Huang, CW ;
Ran, YF ;
Liu, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3406-3412
[20]  
Patel S. J., 2003, ANGEW CHEM, V115, P1402