Alpha-fluoro-alpha-nitro(phenylsulfonyl)methane as a fluoromethyl pronucleophile: efficient stereoselective Michael addition to chalcones.
basic_science · Level V
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- Record sourced from PubMed, PMID 19237559.
- Also identified by DOI 10.1073/pnas.0900179106 and PMC identifier 2657402.
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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.
Medical subject headings
- Chalcones