Enantioselective alkylation of β-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts

被引：137

作者：

Park, EJ ^{[1
]}

Kim, MH ^{[1
]}

Kim, DY ^{[1
]}

机构：

[1] Soonchunhyang Univ, Dept Chem, Chungnam 336600, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 20期

关键词：

D O I：

10.1021/jo0401772

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic enantioselective alkylation promoted by a quaternary ammonium salt from cinchonine as a phase transfer catalyst is described. Treatment of cyclo beta-keto esters with alkyl halide under mild reaction conditions afforded the corresponding alpha-alkylated beta-keto esters in moderate to excellent yields with high enantiomeric excesses.

引用

页码：6897 / 6899

页数：3

共 58 条

[11]

2-V

[12] CHIRAL MICHAEL ADDITION - METHYL VINYL KETONE ADDITION CATALYZED BY CINCHONA ALKALOID DERIVATIVES [J].

CONN, RSE ;

LOVELL, AV ;

KARADY, S ;

WEINSTOCK, LM .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (24) :4710-4711

[13] 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

[14] 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

[15] 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

[16]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO

[17]

2-V

[18]

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

[19]

2-4

[20] 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

← 1 2 3 4 5 6 →