LANTHANOID TRIFLATE CATALYZED CONJUGATE ADDITION OF AMINES TO ALPHA,BETA-UNSATURATED ESTERS - A FACILE ROUTE TO OPTICALLY-ACTIVE BETA-LACTAM

被引：125

作者：

MATSUBARA, S ^{[1
]}

YOSHIOKA, M ^{[1
]}

UTIMOTO, K ^{[1
]}

机构：

[1] KYOTO UNIV, FAC ENGN, DIV MAT SCI, SAKYO KU, KYOTO 60601, JAPAN

来源：

CHEMISTRY LETTERS | 1994年 / 05期

关键词：

D O I：

10.1246/cl.1994.827

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic amount of lanthanoid(III) triflates promoted the conjugate addition of amines to 2-alkenoic acid esters to give beta-amino esters. The reaction of benzylamine with alpha,beta-unsaturated esters containing a stereogenic center at gamma-position proceeded diastereoselectivity to yield optically active beta-lactam precursors.

引用

页码：827 / 830

页数：4

共 23 条

[1] LITHIUM N-BENZYLTRIMETHYLSILYLAMIDE (LSA) - A NEW REAGENT FOR CONJUGATE ADDITION ENOLATE TRAPPING REACTIONS [J].

ASAO, N ;

UYEHARA, T ;

YAMAMOTO, Y .

TETRAHEDRON, 1988, 44 (13) :4173-4180

[2] ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ESTERS THROUGH HIGH-PRESSURE-INDUCED ADDITION OF AMINES TO ALPHA,BETA-ETHYLENIC ESTERS [J].

DANGELO, J ;

MADDALUNO, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8112-8114

[3]

ELIEL EL, 1987, ORG SYNTH, V65, P215

[4] USE OF LANTHANIDE(III) IONS AS CATALYSTS FOR THE REACTIONS OF AMINES WITH NITRILES [J].

FORSBERG, JH ;

SPAZIANO, VT ;

BALASUBRAMANIAN, TM ;

LIU, GK ;

KINSLEY, SA ;

DUCKWORTH, CA ;

POTERUCA, JJ ;

BROWN, PS ;

MILLER, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1017-1021

[5]

FORSBERG JH, 1976, J CHEM SOC CHEM COMM, P106

[6]

FURUKAWA M, 1977, CHEM PHARM BULL, V25, P1319

[7]

IKOTA N, 1985, CHEM PHARM BULL, V33, P3299

[8]

Kleinman E. F., 1991, COMPREHENSIVE ORGANI, P893

[9] ASYMMETRIC REACTIONS BASED ON 1,3-OXATHIANES .3. SECONDARY ALPHA-HYDROXYACIDS, RCHOHCO2H AND GLYCOLS RCHOHCH2OH [J].

KO, KY ;

FRAZEE, WJ ;

ELIEL, EL .

TETRAHEDRON, 1984, 40 (08) :1333-1343

[10] THE ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES IN AQUEOUS-MEDIA [J].

KOBAYASHI, S ;

HACHIYA, I .

TETRAHEDRON LETTERS, 1992, 33 (12) :1625-1628

← 1 2 3 →