Catalytic asymmetric reaction of lithium ester enolates with imines

被引：63

作者：

Tomioka, K ^{[1
]}

Fujieda, H

Hayashi, S

Hussein, MA

Kambara, T

Nomura, Y

Kanai, M

Koga, K

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Univ Tokyo, Grad Sch Pharmaceut Sci, Tokyo 1130033, Japan

[3] Osaka Univ, ISIR, Osaka 5670047, Japan

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 08期

关键词：

D O I：

10.1039/a901424a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An external chiral tridentate amino diether ligand 7 catalyzed the condensation reaction of a lithium ester enolate 2 with an imine 3 to give the enantiomerically enriched beta-lactam 4 in high yield.

引用

页码：715 / 716

页数：2

共 18 条

[1] ARENETRICARBONYLCHROMIUM COMPLEXES AS CHIRAL AUXILIARIES - ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS [J].

BALDOLI, C ;

DELBUTTERO, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (14) :982-984

[2] ASYMMETRIC-SYNTHESIS AND REACTIONS OF CIS-N-(P-TOLUENESULFINYL)AZIRIDINE-2-CARBOXYLIC ACIDS [J].

DAVIS, FA ;

ZHOU, P ;

REDDY, GV .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3243-3245

[3] Ligand-mediated addition of organometallic reagents to azomethine functions [J].

Denmark, SE ;

Nicaise, OJC .

CHEMICAL COMMUNICATIONS, 1996, (09) :999-1004

[4] Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond [J].

Enders, D ;

Reinhold, U .

TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :1895-1946

[5] Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts [J].

Ferraris, D ;

Young, B ;

Dudding, T ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4548-4549

[6] A ternary complex reagent for an asymmetric reaction of lithium ester enolates with imines [J].

Fujieda, H ;

Kanai, M ;

Kambara, T ;

Iida, A ;

Tomioka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (08) :2060-2061

[7]

FUJIOKA H, 1992, SYNLETT, P35

[8] Enantioselective addition of enol silyl ethers to imines catalyzed by palladium complexes: A novel way to optically active acylalanine derivatives [J].

Hagiwara, E ;

Fujii, A ;

Sodeoka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (10) :2474-2475

[9] THE ESTER ENOLATE IMINE CONDENSATION ROUTE TO BETA-LACTAMS [J].

HART, DJ ;

HA, DC .

CHEMICAL REVIEWS, 1989, 89 (07) :1447-1465

[10] HIGHLY SELECTIVE AND OPERATIONALLY SIMPLE SYNTHESIS OF ENANTIOMERICALLY PURE BETA-AMINO ESTERS VIA DOUBLE STEREODIFFERENTIATION [J].

HATTORI, K ;

MIYATA, M ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :1151-1152

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