Formation of Enantiomerically Pure 1??Fluorovinyl and 1??Fluoromethyl Sulfoxides

…, HA van der Hoeven, A van der Gen

Index: Van Steenis, Jan Hein; Boer, Philip W. S.; Van Der Hoeven, Harald A.; Van Der Gen, Arne European Journal of Organic Chemistry, 2001 , # 5 p. 911 - 918

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Citation Number: 7

Abstract

Abstract (SS)-[Fluoro (p-tolylsulfinyl) methyl] diphenylphosphane oxide (2) was obtained with complete stereoselectivity from (fluoromethyl) diphenylphosphane oxide (3) and (S)-(−)- menthyl p-toluenesulfinate. 1-Fluorovinyl p-tolyl sulfoxides 1 were prepared in good yields by Horner− Wittig reaction of 2 with aldehydes, in excellent enantiomeric excess (ee). With ketones, yields were generally low. Stereoselectivity was high for aliphatic aldehydes, ...