STEREOSELECTIVE SYNTHESIS OF 2,5-DIHYDROFURANS BY SEQUENTIAL SN2' CLEAVAGE OF ALKYNYLOXIRANES AND AG+-CATALYZED CYCLIZATION OF THE ALLENYLCARBINOL PRODUCTS

被引：165

作者：

MARSHALL, JA

PINNEY, KG

机构：

[1] Department of Chemistry and Biochemistry, University of South Carolina, Columbia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 25期

关键词：

D O I：

10.1021/jo00077a048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alkynyloxiranes 5a,b, 7, and 18 afford mainly the anti S(N)2' products 6a,b, 8, and 19a upon treatment with Me2CuLi. The derived primary alcohol silyl ethers 9a,b, 10, and 19b-d undergo Ag+-catalyzed cyclization to the 2,5-dihydrofurans 11a,b, 12, and 20b-d. Diol 26 affords mainly the fused ring 2,5-dihydrofuran 32 under these conditions. The stereochemistry of dihydrofuran 20a was confirmed by conversion to the known epoxide 21a.

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页码：7180 / 7184

页数：5

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