ELECTRONIC EFFECTS ON THE STEREOCHEMICAL OUTCOME OF THE PHOTOCHEMICAL-REACTION OF CHROMIUM CARBENE COMPLEXES WITH IMINES TO FORM BETA-LACTAMS

被引：40

作者：

DUMAS, S ^{[1
]}

HEGEDUS, LS ^{[1
]}

机构：

[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 17期

关键词：

D O I：

10.1021/jo00096a046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The results of calculations by Cossio and subsequently Sordo showing that stereoselectivity in the ketene-imine cycloaddition to form p-lactams could be determined by ''torquoelectronic'' effects similar to those used to rationalize cyclobutene ring opening reactions were used to rationalize the contrasteric outcome of over 40 chromium carbene complex-derived alkoxyketene-imine reactions. In addition, the high stereoselectivity observed in these reactions with optically active heterocyclic imines and the unusual instability of azapenams were rationalized using similar arguments.

引用

收藏

页码：4967 / 4971

页数：5

相关论文

共 21 条

[1] THE STEREOSELECTIVE SYNTHESIS OF 3-FLUORO-AZETIDINONES [J].

ARAKI, K ;

WICHTOWSKI, JA ;

WELCH, JT .

TETRAHEDRON LETTERS, 1991, 32 (40) :5461-5464

[2] SYNTHESIS OF AZAPENAMS, DIAZEPINONES, AND DIOXOCYCLAMS VIA THE PHOTOLYTIC REACTION OF CHROMIUM ALKOXYCARBENE COMPLEXES WITH IMIDAZOLINES [J].

BETSCHART, C ;

HEGEDUS, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5010-5017

[3] SYNTHESIS OF AMINO-BETA-LACTAMS BY THE PHOTOLYTIC REACTION OF IMINES WITH PENTACARBONYL[(DIBENZYLAMINO)CARBENE]CHROMIUM(0) [J].

BOREL, C ;

HEGEDUS, LS ;

KREBS, J ;

SATOH, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1101-1105

[4] A SEMIEMPIRICAL THEORETICAL-STUDY ON THE FORMATION OF BETA-LACTAMS FROM KETENES AND IMINES [J].

COSSIO, FP ;

UGALDE, JM ;

LOPEZ, X ;

LECEA, B ;

PALOMO, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :995-1004

[5] CHIRAL CONTROL IN THE STAUDINGER REACTION BETWEEN KETENES AND IMINES - A THEORETICAL SCF-MO STUDY ON ASYMMETRIC TORQUOSELECTIVITY [J].

COSSIO, FP ;

ARRIETA, A ;

LECEA, B ;

UGALDE, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :2085-2093

[6]

Georg GI, 1993, ORGANIC CHEM BETA LA, P295

[7]

HEGEDUS LS, 1985, TETRAHEDRON, V41, P5833, DOI 10.1016/S0040-4020(01)91422-X

[8] REACTION OF CHROMIUM CARBENE COMPLEXES WITH IMINES - SYNTHESIS OF BETA-LACTAMS [J].

HEGEDUS, LS ;

MCGUIRE, MA ;

SCHULTZE, LM ;

YIJUN, C ;

ANDERSON, OP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (09) :2680-2687

[9] EVIDENCE FOR THE INTERMEDIACY OF CHROMIUM KETENE COMPLEXES IN THE SYNTHESIS OF BETA-LACTAMS BY THE PHOTOLYTIC REACTION OF CHROMIUM CARBENE COMPLEXES WITH IMINES - USE IN AMINO-ACID SYNTHESIS [J].

HEGEDUS, LS ;

DEWECK, G ;

DANDREA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2122-2126

[10] A CONTRIBUTION TO THE CONFUSION SURROUNDING THE REACTION OF KETENES WITH IMINES TO PRODUCE BETA-LACTAMS - A COMPARISON OF STEREOSELECTIVITY DEPENDENCE ON THE METHOD OF KETENE GENERATION - ACID CHLORIDE TRIETHYLAMINE VS PHOTOLYSIS OF CHROMIUM CARBENE COMPLEXES [J].

HEGEDUS, LS ;

MONTGOMERY, J ;

NARUKAWA, Y ;

SNUSTAD, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5784-5791