THE UNUSUAL BAEYER-VILLIGER REARRANGEMENT OF BETA-LACTAM ALDEHYDES - TOTALLY STEREOSELECTIVE ENTRY TO CIS-3-SUBSTITUTED 4-FORMYLOXY-2-AZETIDINONES

被引：8

作者：

ALCAIDE, B ^{[1
]}

ALY, MF ^{[1
]}

SIERRA, MA ^{[1
]}

机构：

[1] UNIV ASSIUT,FAC SCI QENA,DEPT CHEM,ASSIUT,EGYPT

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 19期

关键词：

D O I：

10.1016/0040-4039(95)00492-U

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Baeyer-Villiger oxidation of 4-formyl-beta-lactams 1 with m-chloroperbenzoic acid in dichloromethane at room temperature is shown to be a convenient method for the preparation of 4-formyloxy-beta-lactams 2. Some reactions of novel compounds 2 are also described.

引用

收藏

页码：3401 / 3404

页数：4

相关论文

共 26 条

[1] OPTICALLY-ACTIVE FLUORINATED BETA-LACTAM BUILDING-BLOCKS - A NOVEL FLUORINATED RETROAMIDE ISOSTERE [J].

ABOUABDELLAH, A ;

WELCH, JT .

TETRAHEDRON-ASYMMETRY, 1994, 5 (06) :1005-1013

[2] THE STEREOSELECTIVE PREPARATION OF MONO-BETA-LACTAMS AND BIS-BETA-LACTAMS BY THE 1,4-DIAZA 1,3-DIENE-ACID CHLORIDE CONDENSATION - SCOPE AND SYNTHETIC APPLICATIONS [J].

ALCAIDE, B ;

MARTINCANTALEJO, Y ;

PEREZCASTELLS, J ;

RODRIGUEZLOPEZ, J ;

SIERRA, MA ;

MONGE, A ;

PEREZGARCIA, V .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5921-5931

[3] A NOVEL, GENERAL, TOTALLY STEREOSELECTIVE ONE-POT SYNTHESIS OF CIS-3-SUBSTITUTED 4-FORMYLAZETIDIN-2-ONES [J].

ALCAIDE, B ;

MARTINCANTALEJO, Y ;

PLUMET, J ;

RODRIGUEZLOPEZ, J ;

SIERRA, MA .

TETRAHEDRON LETTERS, 1991, 32 (06) :803-806

[4] REAGENTS AND SYNTHETIC METHODS .67. PREPARATION OF 4-UNSUBSTITUTED BETA-LACTAMS FROM 4-ACETOXYAZETIDIN-2-ONES - A FORMAL APPROACH TO MONOBACTAMS AND NOCARDINCINS [J].

ARRIETA, A ;

LECEA, B ;

COSSIO, FP ;

PALOMO, C .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3784-3791

[5] REAGENTS AND SYNTHETIC METHODS .68. AN EXTENSION OF BARRET PROCEDURE FOR THE PREPARATION OF POTENTIALLY VALUABLE CARBAPENEM INTERMEDIATES [J].

ARRIETA, A ;

COSSIO, FP ;

GARCIA, JM ;

LECEA, B ;

PALOMO, C .

TETRAHEDRON LETTERS, 1988, 29 (25) :3129-3132

[6] STUDIES ON LACTAMS .7. A NEW SYNTHESIS OF BETA-AMINO-BETA-LACTAMS [J].

BOSE, AK ;

KUGAJEVS.I .

TETRAHEDRON, 1967, 23 (02) :957-&

[7] STEREOSELECTIVE CHIRAL SYNTHESIS OF N-ARYL-ALPHA-AMINO-BETA-LACTAMS FROM BETA-HYDROXY-ALPHA-AMINO ACIDS [J].

BOSE, AK ;

SAHU, DP ;

MANHAS, MS .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (06) :1229-1230

[8] IMPROVED OXIDATION PROCEDURE WITH AROMATIC PEROXYACIDS [J].

CAMPS, F ;

COLL, J ;

MESSEGUER, A ;

PERICAS, MA .

TETRAHEDRON LETTERS, 1981, 22 (39) :3895-3896

[9] REGIOSELECTIVE BAEYER-VILLIGER REACTION OF POLYHYDROXYCYCLOHEXANONE DERIVATIVES [J].

CHIDA, N ;

TOBE, T ;

OGAWA, S .

TETRAHEDRON LETTERS, 1994, 35 (39) :7249-7252

[10] THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .5. APPLICATION OF CHIRAL ALPHA,BETA-EPOXYIMINES IN KETENE-IMINE CYCLO-ADDITION REACTIONS LEADING TO HOMOCHIRAL 3-AMINOAZETIDINONES [J].

EVANS, DA ;

WILLIAMS, JM .

TETRAHEDRON LETTERS, 1988, 29 (40) :5065-5068