Assessment of the absolute configuration of a series of (3R)-3-hydroxy-3-alkyl-β-lactams

被引：14

作者：

Barbaro, G

Battaglia, A

Guerrini, A

Bertucci, C

Geremia, S

机构：

[1] Univ Pisa, CNR, Ctr Studio Macromol Stereordinate & Otticamente A, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy

[2] CNR, Ist Composti Carbonio Contenenti Eteroatom ICoCEA, I-40129 Bologna, Italy

[3] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 19期

关键词：

D O I：

10.1016/S0957-4166(98)00357-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The absolute stereochemistry of a series of (3R)-3-hydroxy-3-alkyl-beta-lactams has been determined by circular dichroism and NMR spectroscopies. The sign of the circular dichroism band between 250 and 220 nm was related to the stereochemistry by applying the beta-lactam sector rule. The NMR analysis unambiguously determines the relative configuration at C3 and C4 of the beta-lactam ring. The reliability of the method has been proved by X-ray analysis of two of the examined compounds. The obtained results are in agreement with the mechanism proposed for the employed synthetic route. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3401 / 3409

页数：9

共 25 条

[1] HIGH-PRESSURE-PROMOTED (2 + 2) CYCLOADDITIONS OF IMINES WITH ELECTRON-RICH ALKENES - A SIMPLE ROUTE TO AZETIDINES AND BETA-AMINO CARBONYL-COMPOUNDS [J].

ABEN, RWM ;

SMIT, R ;

SCHEEREN, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03) :365-370

[2] 2-IMINOOXETANE CHEMISTRY .2. GENERAL-SYNTHESIS FROM KETENE IMINE ALDEHYDE CYCLO-ADDITIONS [J].

BARBARO, G ;

BATTAGLIA, A ;

GIORGIANNI, P .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5501-5506

[3] One-pot synthesis of (3R)-hydroxy-beta-lactams via enolates of 2-tert-butyl-1,3-dioxolan-4-ones .1. [J].

Barbaro, G ;

Battaglia, A ;

Guerrini, A ;

Bertucci, C .

TETRAHEDRON-ASYMMETRY, 1997, 8 (15) :2527-2531

[4]

BATTAGLIA A, UNPUB

[5]

BENTLEY PH, 1988, RECENT ADV CHEM BETA

[6]

BOSE AK, 1974, TETRAHEDRON LETT, V36, P3135

[7] ELECTRONIC-STRUCTURES OF CEPHALOSPORINS AND PENICILLINS .8. CHIROPTICAL PROPERTIES OF 1-CARBAPENAM AND ORBITAL MIXING IN NONPLANAR AMIDES [J].

BOYD, DB ;

RIEHL, JP ;

RICHARDSON, FS .

TETRAHEDRON, 1979, 35 (12) :1499-1508

[8]

CHRISTENSEN BG, 1981, STRUCTURE ACTIVITY R

[9]

COSSIO FP, 1985, TETRAHEDRON LETT, V35, P4239

[10] DOCETAXEL (TAXOTERE) DERIVATIVES - NOVEL NBCL3-BASED STEREOSELECTIVE APPROACH TO 2'-METHYLDOCETAXEL [J].

DENIS, JN ;

FKYERAT, A ;

GIMBERT, Y ;

COUTTEREZ, C ;

MANTELLIER, P ;

JOST, S ;

GREENE, AE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (14) :1811-1815

← 1 2 3 →