STEREOSELECTIVE SAMARIUM DIIODIDE-PROMOTED INTERMOLECULAR COUPLING OF ALKYNYLOXIRANES WITH KETONES - SYNTHESIS OF 2,3-PENTADIENE-1,5-DIOLS

被引：21

作者：

AURRECOECHEA, JM

SOLAY, M

机构：

[1] Departmento de Química Orgánica, Facultad de Ciencias, Universidad del Pafs Vasco, 48080 Bilbao

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 14期

关键词：

D O I：

10.1016/0040-4039(95)00254-A

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of samarium diiodide (SmI2), alkynyloxiranes undergo an efficient reductive coupling with ketones to afford 2,3-pentadiene-1,5-diols. The isolated yields are high and the stereoselectivity of the process ranges from moderate to very high. The stereochemistry of the major product of the reaction is the result of the new C-C bond forming anti with respect to the opening epoxide ring.

引用

页码：2501 / 2504

页数：4

共 19 条

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