Asymmetric Nucleophilic Monofluorobenzylation of Allyl and Propargyl Halides Mediated by a Remote Sulfinyl Group: Synthesis of Homoallylic and Homopropargylic Fluorides

作者:Arroyo Yolanda; Ascension Sanz Tejedor M; Parra Alejandro; Alonso Ines; Garcia Ruano Jose Luis
来源:Journal of Organic Chemistry, 2014, 79(15): 6970-6977.
DOI:10.1021/jo501096f

摘要

Fluorinated 2(p-tolylsulfinyl)benzyl carbanions react with allyl and propargyl halides in a highly stereoselective way, providing homoallylic and homopropargylic fluorides, respectively, with high optical purity. Theoretical calculations found transition states for these transformations whose relative stabilities are consistent with the experimentally observed stereoselectivity.

  • 出版日期2014-8-1