Highly enantioselective Michael reactions catalyzed by a chiral quaternary ammonium salt.: Illustration by asymmetric syntheses of (S)-ornithine and chiral 2-cyclohexenones

被引:177
作者
Zhang, FY [1 ]
Corey, EJ [1 ]
机构
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
关键词
D O I
10.1021/ol0056527
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of the chiral quaternary ammonium salts 1a and 1b makes possible enantioselective Michael reactions which have been applied to the asymmetric syntheses of (S) ornithine (2) and the chiral 2-cyclohexenone 6.
引用
收藏
页码:1097 / 1100
页数:4
相关论文
共 13 条
[1]   SYNTHESIS OF L-ORNITHINES STEREOSPECIFICALLY DEUTERATED AT C-3 [J].
BALDWIN, JE ;
MERRITT, KD ;
SCHOFIELD, CJ .
TETRAHEDRON LETTERS, 1993, 34 (24) :3919-3920
[2]   Mechanism and conditions for highly enantioselective epoxidation of α,β-enones using charge-accelerated catalysis by a rigid quaternary ammonium salt [J].
Corey, EJ ;
Zhang, FY .
ORGANIC LETTERS, 1999, 1 (08) :1287-1290
[3]   Highly enantioselective phase transfer catalyzed alkylation of a 3-oxygenated propionic ester equivalent; applications and mechanism [J].
Corey, EJ ;
Bo, YX ;
Busch-Petersen, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :13000-13001
[4]   Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst [J].
Corey, EJ ;
Noe, MC ;
Xu, F .
TETRAHEDRON LETTERS, 1998, 39 (30) :5347-5350
[5]  
Corey EJ, 1999, ANGEW CHEM INT EDIT, V38, P1931, DOI 10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO
[6]  
2-4
[7]   A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].
Corey, EJ ;
Xu, F ;
Noe, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415
[8]   Transformations of isoxazolidine and dihydropyran derivatives to optically active compounds [J].
DiazOrtiz, A ;
DiezBarra, E ;
delaHoz, A ;
Prieto, P ;
Moreno, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (03) :259-263
[9]   THE MECHANISM OF SODIUM-BOROHYDRIDE COBALTOUS CHLORIDE REDUCTIONS [J].
HEINZMAN, SW ;
GANEM, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (24) :6801-6802
[10]   Enantioselective synthesis of β-hydroxy-α-amino acid esters by aldol coupling using a chiral quaternary ammonium salt as catalyst [J].
Horikawa, M ;
Busch-Petersen, J ;
Corey, EJ .
TETRAHEDRON LETTERS, 1999, 40 (20) :3843-3846