DIASTEREOFACIAL SELECTIVITY OF THE CYCLOADDITION OF DIAZO-COMPOUNDS TO ENONES

被引：33

作者：

GALLEY, G

PATZEL, M

JONES, PG

机构：

[1] HUMBOLDT UNIV BERLIN,FACHBEREICH CHEM,D-10115 BERLIN,GERMANY

[2] TECH UNIV CAROLO WILHELMINA BRAUNSCHWEIG,INST ANORGAN & ANALYT CHEM,D-38023 BRAUNSCHWEIG,GERMANY

来源：

TETRAHEDRON | 1995年 / 51卷 / 06期

关键词：

D O I：

10.1016/0040-4020(94)01049-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral alpha,beta-unsaturated gamma-allroxy- or gamma-amino-ketones (enones) 1 react with diazo compounds in a stereoselective manner affording conjugated Delta(2)-pyrazolines 5 and 6. In all cases syn-selectivity for the cycloaddition was observed. The diastereomeric ratio is improved at lower temperatures, but no significant influence of high pressure is observed. Carrying out this reaction with (E) and (Z) derivatives of the same enone 1 leads to identical products.

引用

页码：1631 / 1640

页数：10

共 37 条

[1] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES ON ENANTIOMERICALLY PURE (E)-GAMMA-ALKOXY-ALPHA,BETA-UNSATURATED ESTERS
ANNUNZIATA, R
CINQUINI, M
COZZI, F
RAIMONDI, L
PILATI, T
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1329 - 1342
[2] ANNUNZIATA R, 1993, TETRAHEDRON, V38, P8629
[3] [Anonymous], 1991, ANGEW CHEM, V103, P1559
[4] ORIGIN OF PI-FACIAL STEREOSELECTIVITY IN ADDITIONS TO PI-BONDS - GENERALITY OF THE ANTI-PERIPLANAR EFFECT
CARAMELLA, P
RONDAN, NG
PADDONROW, MN
HOUK, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) : 2438 - 2440
[5] Carruthers W., 2013, CYCLOADDITION REACTI
[6] DEBOER TJ, 1963, ORG SYNTH, V4, P250
[7] OPTICALLY-ACTIVE C5-SYNTHONS FOR THE SYNTHESIS OF NATURALLY-OCCURRING TERPENES
DUMONT, R
PFANDER, H
[J]. HELVETICA CHIMICA ACTA, 1983, 66 (03) : 814 - 823
[8] Galley G. R., UNPUB
[9] HAFELE B, 1987, LIEBIGS ANN CHEM, P85
[10] ALLYLIC 1,3-STRAIN AS A CONTROLLING FACTOR IN STEREOSELECTIVE TRANSFORMATIONS
HOFFMANN, RW
[J]. CHEMICAL REVIEWS, 1989, 89 (08) : 1841 - 1860

← 1 2 3 4 →