THE EFFECT OF POLAR SUBSTITUENTS ON THE CONFORMATION AND STEREOCHEMISTRY OF ENOLATE RADICALS

被引：43

作者：

GIESE, B

DAMM, W

WETTERICH, F

ZEITZ, HG

RANCOURT, J

GUINDON, Y

机构：

[1] BIOMEGA BOEHRINGER INGELHEIM RES INC, LAVAL H7S 2G5, PQ, CANADA

[2] UNIV MONTREAL, DEPT CHEM, MONTREAL H7S 2G5, PQ, CANADA

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 37期

关键词：

D O I：

10.1016/S0040-4039(00)73805-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

ESR measurements and AM1 calculations show that ester substituted radicals 2 and 6 prefer conformation A as a result of allylic strain effects. But dipolar repulsion between substituents X and CO2Et in 2 and 6 has a pronounced effect on the conformation and the stereoselectivity of radicals 2 and 6.

引用

页码：5885 / 5888

页数：4

共 11 条

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[2] STEREOSELECTIVE HYDROGEN-TRANSFER REACTIONS INVOLVING ACYCLIC RADICALS - A STUDY OF RADICAL CONFORMATIONS USING SEMIEMPIRICAL CALCULATIONS
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[5] 1,2-STEREOINDUCTION IN ACYCLIC RADICALS - ALLYLIC STRAIN EFFECTS
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[J]. TETRAHEDRON LETTERS, 1992, 33 (14) : 1863 - 1866
[6] STEREOSELECTIVE RADICAL-MEDIATED REDUCTION AND ALKYLATION OF ALPHA-HALO ESTERS
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[J]. TETRAHEDRON LETTERS, 1991, 32 (01) : 27 - 30
[7] STEREOSELECTIVE REDUCTION OF ACYCLIC ALPHA-BROMO ESTERS
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[J]. TETRAHEDRON LETTERS, 1990, 31 (20) : 2845 - 2848
[8] HART DJ, 1991, SYNLETT, P412
[9] INVESTIGATION OF A MODEL FOR 1,2-ASYMMETRIC INDUCTION IN REACTIONS OF ALPHA-CARBALKOXY RADICALS - A STEREOCHEMICAL COMPARISON OF REACTIONS OF ALPHA-CARBALKOXY RADICALS AND ESTER ENOLATES
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[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (16) : 4457 - 4470
[10] RADICAL REARRANGEMENT OF 2-O-(DIPHENYLPHOSPHORYL)GLYCOSYL BROMIDES - A NEW SYNTHESIS FOR 2-DEOXY DISACCHARIDES AND 2-DEOXY RIBONUCLEOSIDES
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