Chiral Fluorinated α??Sulfonyl Carbanions: Enantioselective Synthesis and Electrophilic Capture, Racemization Dynamics, and Structure

G Hellmann, A Hack, E Thiemermann…

Index: Hellmann, Gunther; Hack, Achim; Thiemermann, Eric; Luche, Olaf; Raabe, Gerhard; Gais, Hans-Joachim Chemistry - A European Journal, 2013 , vol. 19, # 12 p. 3869 - 3897

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Citation Number: 11

Abstract

Abstract Enantiomerically pure triflones R 1 CH (R 2) SO 2 CF 3 have been synthesized starting from the corresponding chiral alcohols via thiols and trifluoromethylsulfanes. Key steps of the syntheses of the sulfanes are the photochemical trifluoromethylation of the thiols with CF 3 Hal (Hal= halide) or substitution of alkoxyphosphinediamines with CF 3 SSCF 3. The deprotonation of RCH (Me) SO 2 CF 3 (R= CH 2 Ph, iHex) with nBuLi with the ...