Cascade Michael-Aldol reactions promoted by hydrogen bonding mediated catalysis

被引:254
作者
Zu, Liansuo [1 ]
Wang, Jian [1 ]
Li, Hao [1 ]
Xie, Hexin [1 ]
Jiang, Wei [1 ]
Wang, Wei [1 ]
机构
[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA
关键词
D O I
10.1021/ja067781+
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly enantio- and diastereoselective tandem Michael-aldol reactions, efficiently catalyzed by a cinchona alkaloid thiourea via synergistic noncovalent hydrogen-bonding activation of both the Michael donor and acceptor, have been developed. The process affords a powerful means for the construction of versatile chiral thiochromanes with the formation of three stereogenic centers in a one-pot synthesis from simple achiral compounds.
引用
收藏
页码:1036 / 1037
页数:2
相关论文
共 42 条
[1]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[2]   Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts [J].
Berkessel, A ;
Cleemann, F ;
Mukherjee, S ;
Müller, TN ;
Lex, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) :807-811
[3]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[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]   Direct amino acid catalyzed asymmetric synthesis of polyketide sugars [J].
Casas, J ;
Engqvist, M ;
Ibrahem, I ;
Kaynak, B ;
Córdova, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1343-1345
[6]   Organocatalysis mediated by (thio)urea derivatives [J].
Connon, Stephen J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5418-5427
[7]   ALTERING THE STEREOCHEMISTRY OF ALLYLATION REACTIONS OF CYCLIC ALPHA-SULFINYL RADICALS WITH DIARYLUREAS [J].
CURRAN, DP ;
KUO, LH .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3259-3261
[8]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175
[9]   A catalyst that plays multiple roles:: Asymmetric synthesis of β-substituted aspartic acid derivatives through a four-stage, one-pot procedure [J].
Dudding, T ;
Hafez, AM ;
Taggi, AE ;
Wagerle, TR ;
Lectka, T .
ORGANIC LETTERS, 2002, 4 (03) :387-390
[10]   Control of four stereocentres in a triple cascade organocatalytic reaction [J].
Enders, Dieter ;
Hüettl, Matthias R. M. ;
Grondal, Christoph ;
Raabe, Gerhard .
NATURE, 2006, 441 (7095) :861-863