Tetrahedron

Synthesis of allenic diols by samarium diiodide-promoted coupling between alkynyloxiranes and ketones

JM Aurrecoechea, E Alonso, M Solay

Index: Aurrecoechea, Jose M.; Alonso, Eva; Solay, Monica Tetrahedron, 1998 , vol. 54, # 15 p. 3833 - 3850

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Citation Number: 21

Abstract

The SmI2-mediated reductive coupling between alkynyloxiranes and ketones provides a new route to 2, 3-pentadiene-1, 5-diols. The preferred stereochemistry observed in the coupling products is the result of the new C C bond forming anti with respect to the opening epoxide ring. Yields and diastereoselectivities are dependent on the alkynyloxirane substitution pattern.