ENANTIOSELECTIVE SYNTHESIS OF HYDROXYALKYLCYCLOPROPANECARBOXYLIC ACID-DERIVATIVES

被引：13

作者：

BARTELS, A ^{[1
]}

LIEBSCHER, J ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 08期

关键词：

D O I：

10.1016/0957-4166(94)80109-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 [无机化学]; 081704 [应用化学];

摘要：

Cycloaddition of diazomethane to enantiomerically pure 5-alkylidene-1,3-dioxane-4-ones 1 affords spiropyrazolines 2. Upon irradiation these products loose N-2 giving cyclopropanes 3 that are spiro annellated to the 5-position of the 1,3-dioxane-4-one ring. Both transformations are highly stereoselective giving rise to essentially pure enantiomers in quantitative yields.

引用

页码：1451 / 1452

页数：2

共 5 条

[1]

ENANTIOSELECTIVE SYNTHESIS OF (+)-(1R,2S)-ALLOCORONAMIC ACID [J].

ALCARAZ, C ;

HERRERO, A ;

MARCO, JL ;

FERNANDEZALVAREZ, E ;

BERNABE, M .

TETRAHEDRON LETTERS, 1992, 33 (38) :5605-5608

[2]

(2R)-5-ALKYL-2-TERT-BUTYL-6-METHYL-4H-1,3-DIOXIN-4-ONES AS INTERMEDIATES FOR THE PREPARATION OF ALPHA-BETA-BETA-TRISUBSTITUTED BETA-HYDROXYCARBOXYLIC ACIDS FROM (R)-3-HYDROXYBUTYRIC ACID UNDER SELF-REGENERATION OF THE STEREOGENIC CENTER [J].

AMBERG, W ;

SEEBACH, D .

CHEMISCHE BERICHTE, 1990, 123 (12) :2429-2438

[3]

(E,R,R)-5-ALKYLIDENE-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONES - PREPARATION FROM (R)-3-HYDROXYBUTYRIC ACID, CUPRATE ADDITIONS, AND HYDROLYZES TO 3-HYDROXYCARBOXYLIC ACIDS WITH CHIRAL SECONDARY ALKYL SUBSTITUENTS IN THE 2-POSITION [J].

AMBERG, W ;

SEEBACH, D .

CHEMISCHE BERICHTE, 1990, 123 (12) :2413-2428

[4]

1,2-STEREOINDUCTION IN RADICAL REACTIONS - STEREOSELECTIVE SYNTHESIS OF 2-ALKYL-3-HYDROXYBUTANOATES [J].

BULLIARD, M ;

ZEHNDER, M ;

GIESE, B .

HELVETICA CHIMICA ACTA, 1991, 74 (07) :1600-1607

[5]

MAAS G, 1987, TOP CURR CHEM, V137, P75

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