Tetrahedron p. 6553 - 6564 (1990)
Update date:2022-09-26
Topics:
Saengchantara, Suthiweth T.
Wallace, Timothy W.
3-(p-Tolylsulphinyl)chromone 3a undergoes diastereoselective conjugate addition of lithium dimethylcuprate, producing a mixture of 2-methyl-3-(p-tolylsulphinyl)chroman-4-ones. Heating the mixture to 140°C gives 2-methylchromone in quantitative yield. Desulphurisation of the mixed products from (S)-3a gives (S)-2-methylchroman-4-one with 90% e.e. Chelation of the carbonyl and sulphoxide oxygens during methyl addition accounts for the diastereo selection.
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