Tetrahedron

Efficient routes to cyclic 2, 3-epoxyalcohols from cycloalkenyl ketones, via cycloalkenyl alcohols

…, AJ Walker, J Pickering, S Harper, R Wrigglesworth…

Index: Marson; Walker; Pickering; Harper; Wrigglesworth; Edge Tetrahedron, 1993 , vol. 49, # 45 p. 10317 - 10338

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Citation Number: 12

Abstract

The minimising of torsional strain and non-bonding interactions is proposed as the explanation of high diastereoselectivity observed in the epoxidation of cycloalkenyl alcohols, reported for twenty three examples. The resulting 2, 3-epoxyalcohols are key intermediates in the synthesis of tricyclic 1, 2-diols and β-hydroxy ketones.

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