STEALTH STEREOCONTROL - STEREOCHEMICAL REVERSAL OF A MICHAEL ADDITION-REACTION

被引：22

作者：

BARRETT, AGM ^{[1
]}

WEIPERT, PD ^{[1
]}

DHANAK, D ^{[1
]}

HUSA, RK ^{[1
]}

LEBOLD, SA ^{[1
]}

机构：

[1] NORTHWESTERN UNIV,DEPT CHEM,EVANSTON,IL 60208

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 26期

关键词：

D O I：

10.1021/ja00026a016

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The nitroalkene, methyl 5,6-dideoxy-2,3-O-isopropylidene-6-nitro-6-(phenylthio)-beta-D-ribo-hex-5(Z)-enofuranoside (1), was found to react with nucleophiles to give, on ozonolysis, the corresponding phenyl thiolesters 3, 5, 6a-c, and 7 bearing the nucleophilic residue alpha to the carbonyl group. The nucleophiles Me3SiOK, NaOMe, NaOCH2Ph, and TsNHK all stereoselectively (7:1-50:1) reacted to give products with the allo-thiouronate configuration. In contrast, potassium succinimide and phthalimide, nucleophiles with aerofoil bulk, gave substituted talo-thiouronates (> 15:1).

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页码：9820 / 9824

页数：5

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