Hydrozirconation VI: selective reduction of epoxides

Abstract

Epoxides undergo hydrozirconation under mild conditions. The reaction intermediates, alkoxylbis(cyclopentadienyl)zirconium chlorides, are easily decomposed by moisture. The hydrozirconation of epoxides to alcs. shows high regioselectivity which can exceed 92% for aromatic epoxides. In contrast to LiAlH4, the results of hydrozirconation of epoxides to alcs. are similar to electrophilic metal hydride reduction, which gives predominantly less substituted alcs. Addition of Cp2MCl2 (M = Ti, Zr), or Ti(OBu)4 improved the regioselectivity of hydrozirconation but decreased the regioselectivity with LiAlH4.

Key words: HYDROZIRCONATION, EPOXIDE, ALUMINIUM LITHIUM HYD, SELECTIVE REDUCTION

CLC Number:

O627

Cite this article

WANG JITAO;ZHANG YUNWEN;XU YUMING;BAI ANCAI. Hydrozirconation VI: selective reduction of epoxides[J]. Chin. J. Org. Chem., 1989, 9(1): 41-44.

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