Diastereoselective oxygen to carbon rearrangements of anomerically linked enol ethers and the total synthesis of (+)-(S, S)-(cis-6-methyltetrahydropyran-2-yl) acetic …

DJ Dixon, SV Ley, EW Tate

Index: Dixon, Darren J.; Ley, Steven V.; Tate, Edward W. Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 15 p. 2385 - 2394

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Citation Number: 47

Abstract

A range of enol ethers, linked via their oxygen atom to the anomeric centre of a pyran ring system, was shown to undergo oxygen to carbon rearrangement upon treatment with a Lewis acid to give the corresponding 2-carbon substituted products. At low temperature, trimethylsilyl trifluoromethanesulfonate catalysed rearrangements of anomerically linked 6-substituted tetrahydropyranyl enol ethers gave selectively the trans-pyranyl ketones, whereas at higher temperatures ...