Generation and trapping of allene oxides: An approach to chiral, nonracemic α-alkoxyketones

M Shipman, HR Thorpe, IR Clemens

Index: Shipman, Michael; Thorpe, Heidi R.; Clemens, Ian R. Tetrahedron, 1998 , vol. 54, # 47 p. 14265 - 14282

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Citation Number: 9

Abstract

Epoxy mesylates 5 react with a variety of sodium alkoxides to produce the corresponding α- alkoxyketones in good yields. Evidence is presented for the involvement of transient allene oxides in these reactions. Enantiomerically enriched epoxy mesylates (2R, 3S)-5a-c were prepared using the Sharpless asymmetric epoxidation reaction as the key step. These precursors rearrange to α-alkoxyketones without significant racemisation under modified ...