The wittig rearrangement as a practical method for aldehyde synthesis

M Schlosser, S Strunk

Index: Schlosser, Manfred; Strunk, Sven Tetrahedron, 1989 , vol. 45, # 9 p. 2649 - 2664

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Citation Number: 36

Abstract

If the rearrangement of metalated allyl ethers 2 (or 4) is accomplished in the presence of potassium tert-butoxide, primary alkyl groups preferentially migrate to the unsubstituted allylic terminus (γ-position). Enolates 7 and 1-vinylalcoholates 6 (by alkyl migration to the α- position, adjacent to the oxygen atom) are produced in an approximate ratio of 9: 1. Because of the endo-configuration of their organometallic precursors, the enolates exclusively ...