Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones

被引:663
作者
Burstein, C [1 ]
Glorius, F [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim An Der Ruhr, Germany
关键词
aldehydes; carbene; heterocycles; organocatalysis; umpolung;
D O I
10.1002/anie.200461572
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Advantage organocatalysis: N-heterocyclic carbenes can generate homoenolate equivalents under mild conditions by conjugate umpolung of α,β- unsaturated aldehydes. This organocatalytic reaction allows an efficient one-step synthesis of substituted γ-butyrolactones 1 (see scheme, Mes = mesityl).
引用
收藏
页码:6205 / 6208
页数:4
相关论文
共 58 条
[11]   Nucleophilic carbenes in asymmetric organocatalysis [J].
Enders, D ;
Balensiefer, T .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :534-541
[12]  
Enders D, 2002, ANGEW CHEM INT EDIT, V41, P1743, DOI 10.1002/1521-3773(20020517)41:10<1743::AID-ANIE1743>3.0.CO
[13]  
2-Q
[14]  
Enders D, 1998, ANGEW CHEM INT EDIT, V37, P1673, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1673::AID-ANIE1673>3.0.CO
[15]  
2-A
[16]   The first asymmetric intramolecular Stetter reaction [J].
Enders, D ;
Breuer, K ;
Runsink, J ;
Teles, JH .
HELVETICA CHIMICA ACTA, 1996, 79 (07) :1899-1902
[17]  
Enders D., 1998, ANGEW CHEM, V110, P1770
[18]  
Enders D., 2002, ANGEW CHEM, V114, P1822
[19]  
EVANS DA, 1973, TETRAHEDRON LETT, P4929
[20]   Oxazolines as chiral building blocks for imidazolium salts and N-heterocyclic carbene ligands [J].
Glorius, F ;
Altenhoff, G ;
Goddard, R ;
Lehmann, C .
CHEMICAL COMMUNICATIONS, 2002, (22) :2704-+