Synthesis of a new family of chiral fluorinated synthons:(R)-and (S)-4-fluoro-1-alkynes

PH Buist, RA Adeney

Index: Buist, Peter H.; Adeney, Reese A. Journal of Organic Chemistry, 1991 , vol. 56, # 10 p. 3449 - 3452

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Citation Number: 10

Abstract

, I (a) KMnO,, H+;(b) LiAlH,;(c)(+)-MTPA C1. acetylide with l, 2-epoxyoctane, was conveniently resolved by chromatographic separation of the corresponding (8)-0- methylmandelate esters to give the two enantiomeric decynols, each in 15% overall yield. The absolute configuration of these alcohols was straightforward to assign since the'H NMR data of the mandelate esters closely matched that reported in the literature for the hexynol ...