Chemische Berichte

Asymmetric Induction in the Wittig??Still Rearrangement of Ethers Containing an Allylic Stereocenter–Diastereocontrol by Allylic Oxygen

H Priepke, R Brückner

Index: Priepke, Henning; Brueckner, Reinhard Chemische Berichte, 1990 , vol. 123, # 1 p. 153 - 168

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Citation Number: 41

Abstract

Stannylated ally1 ethers 13, 15, 19, and 21 bearing an allylic center of chirality are submitted to the Still variant of the [2, 3] Wittig rearrangement. In these reactions alkoxy groups at the chiral center exert stereocontrol through asymmetric induction. With only few exceptions, the syn-configurated rearrangement product (27) is formed in preference to the anti epimer (28). syn: anti ratios are often> 90:< 10 and repeatedly