The use of aqueous dimethylamine as reagent for the regiospecific C4-epimerization of cis-3-substituted 4-formyl-2-azetidinones

被引：7

作者：

Alcaide, B ^{[1
]}

Aly, MF ^{[1
]}

Rodríguez-Vicente, A ^{[1
]}

机构：

[1] Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 32期

关键词：

D O I：

10.1016/S0040-4039(98)01167-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient method for the synthesis of trans-3-substituted 4-formyl-2-azetidinones 2 is described based on the regiospecific C4-epimerization of the cis-isomers 1 using aqueous dimethylamine as reagent in heterogeneous medium. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5865 / 5866

页数：2

共 19 条

[1] Stereoselective synthesis of 3-substituted 4-(formyloxy)-2-azetidinones by the unusual Baeyer-Villiger reaction of beta-lactam aldehydes. Scope and synthetic applications
Alcaide, B
Aly, MF
Sierra, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) : 8819 - 8825
[2] C4,C4'-bis-beta-lactam to fused bis-gamma-lactam rearrangement
Alcaide, B
MartinCantalejo, Y
PerezCastells, J
Sierra, MA
Monge, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9156 - 9163
[3] 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
ALCAIDE, B
MARTINCANTALEJO, Y
PEREZCASTELLS, J
RODRIGUEZLOPEZ, J
SIERRA, MA
MONGE, A
PEREZGARCIA, V
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) : 5921 - 5931
[4] A NOVEL, GENERAL, TOTALLY STEREOSELECTIVE ONE-POT SYNTHESIS OF CIS-3-SUBSTITUTED 4-FORMYLAZETIDIN-2-ONES
ALCAIDE, B
MARTINCANTALEJO, Y
PLUMET, J
RODRIGUEZLOPEZ, J
SIERRA, MA
[J]. TETRAHEDRON LETTERS, 1991, 32 (06) : 803 - 806
[5] ALCAIDE B, 1986, HETEROCYCLES, V24, P1579
[6] STEREOSELECTIVE SYNTHESIS OF AZETIDIN-2-ONES, PRECURSORS OF BIOLOGICALLY-ACTIVE SYN-3-AMINO-2-HYDROXYBUTANOIC ACIDS
ANNUNZIATA, R
BENAGLIA, M
CINQUINI, M
COZZI, F
PONZINI, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) : 4746 - 4748
[7] EPIMERISATION OF TRANS-BETA-LACTAM
BOSE, AK
NARAYANA.CS
MANHAS, MS
[J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (16): : 975 - &
[8] AN IMPROVED ENTRY TO A KEY INTERMEDIATE FOR THIENAMYCIN SYNTHESIS FROM METHYL (R)-3-HYDROXYBUTANOATE VIA DIRECT EPIMERIZATION AT C-3 ON 2-AZETIDINONE RINGS
CHIBA, T
NAKAI, T
[J]. TETRAHEDRON LETTERS, 1985, 26 (38) : 4647 - 4648
[9] 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
EVANS, DA
WILLIAMS, JM
[J]. TETRAHEDRON LETTERS, 1988, 29 (40) : 5065 - 5068
[10] Georg G. I., 1993, The Organic Chemistry of (3-Lactams, P295, DOI [10.1002/chin.199425299, DOI 10.1002/CHIN.199425299]

← 1 2 →