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Updated: Jun 25, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Alpha-fluoro-alpha-nitro(phenylsulfonyl)methane as a fluoromethyl pronucleophile: efficient stereoselective Michael
G K Surya Prakash1, Fang Wang, Timothy Stewart
1Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661, USA. gprakash@usc.edu
Abstract:
Highly efficient stereoselective 1,4-addition of racemic alpha-fluoro-alpha-nitro(phenylsulfonyl)methane (FNSM) as a fluoromethyl pronucleophile to alpha,beta-unsaturated ketones using a wide range of chiral organobifunctional catalysts under moderate conditions in the absence of an additional base has been achieved. A series of catalysts was screened for the enantioselective addition of FNSM to chalcones and the catalysts CN I, CD I, QN I-IV, and QD I were found to enable this reaction, successfully providing exclusive 1,4-addition products stereoselectively in high yields (conversion, diastereomeric ratio, and enantiomeric excess). Studies involving a model reaction and systematic analysis of the absolute configuration support the suggested mechanism.
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