Silyl ketone chemistry. Preparation and reactions of silyl allenol ethers. Diels-Alder reaction of siloxy vinylallenes leading to sesquiterpenes

HJ Reich, EK Eisenhart, RE Olson…

Index: Reich,H.J.; Eisenhart,E.K.; Olson,R.E. Journal of the American Chemical Society, 1986 , vol. 108, p. 7791

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Citation Number: 105

Abstract

Abstract: Allenol silyl ethers 1 with various substitution patterns were prepared. The allene functionality was introduced either by the alkylation of siloxypropargyllithium reagents 3 (Scheme I) or the 0-elimination of 2-halo-1-siloxyallyllithium reagents 4 (Scheme 11). In each case the lithium reagent was formed by a [1, 2]-sigmatropic rearrangement of a suitable cy-silyl alkoxide, which in turn was prepared by addition of alkynyl, vinyl, or other ...