Synthesis of highly functionalized chiral cyclopentanes by catalytic enantio- and diastereoselective double Michael addition reactions

被引:119
作者
Zu, Liansuo
Li, Hao
Xie, Hexin
Wang, Jian
Jiang, Wei
Tang, Yun
Wang, Wei
机构
[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA
[2] E China Univ Sci & Technol, Dept Med Chem, Sch Pharm, Shanghai 200237, Peoples R China
关键词
aldehydes; cyclopentanes; domino reactions; Michael addition; organocatalysis;
D O I
10.1002/anie.200700485
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Do a double take: A novel highly enantio-and diastereoselective cascade double Michael reaction, in which two C-C bonds and three contiguous stereogenic centers are formed, has been developed. The one-pot process, which was efficiently catalyzed by the chiral diphenylprolinyl trimethylsilyl (TMS) ether, is a facile approach to synthetically useful chiral cyclopentanes (see scheme). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3732 / 3734
页数:3
相关论文
共 59 条
[1]   Convenient 'one-pot' synthesis of 3,4-substituted tetrahydrothiophenes through tandem Michael-Henry and Michael-Michael reactions [J].
Barco, Achille ;
Baricordi, Nikla ;
Benetti, Simonetta ;
De Risi, Carmela ;
Pollini, Gian Piero .
TETRAHEDRON LETTERS, 2006, 47 (46) :8087-8090
[2]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[3]   Synthesis and biological activity of prostaglandin analogs containing heteroatoms in the cyclopentane ring [J].
Biaggio, FC ;
Rufino, AR ;
Zaim, MH ;
Zaim, CYH ;
Bueno, MA ;
Rodrigues, A .
CURRENT ORGANIC CHEMISTRY, 2005, 9 (05) :419-457
[4]   Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions [J].
Brandau, Sven ;
Maerten, Eddy ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14986-14991
[5]   Tandem Michael/Michael reactions mediated by phosphines or aryl thiolates [J].
Brown, PM ;
Käppel, N ;
Murphy, PJ .
TETRAHEDRON LETTERS, 2002, 43 (48) :8707-8710
[6]  
CARLONE A, 2007, ANGEW CHEM, V119, P1119
[7]   A new approach for an organocatalytic multicomponent domino asymmetric reaction [J].
Carlone, Armando ;
Cabrera, Silvia ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1101-1104
[8]   Enantioselective organocatalytic aminomethylation of aldehydes:: A role for ionic interactions and efficient access to β2-amino acids [J].
Chi, Yonggui ;
Gellman, Samuel H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6804-6805
[9]  
Dalko P.I., 2004, ANGEW CHEM, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[10]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175