Synthesis of Enantiopure Homoallylic Ethers by Reagent Controlled Facial Selective Allylation of Chiral Ketones

LF Tietze, B Weigand, L Völkel, C Wulff…

Index: Tietze, Lutz F.; Weigand, Berthold; Voelkel, Ludwig; Wulff, Christian; Bittner, Christian Chemistry--A European Journal, 2001 , vol. 7, # 1 p. 161 - 168

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Citation Number: 18

Abstract

Abstract The stereoselective allylation of chiral methyl ketones to give tertiary homoallylic ethers, which can easily be transformed into homoallylic alcohols, is described. Reaction of the enantiopure ketones 8 a–d and the racemic ketones 26 a–d with the norpseudoephedrine derivative 2 or ent-2 and allylsilane in the presence of a catalytic amount of trifluoromethanesulfonic acid, led to a series of homoallylic ethers with good to ...

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