Expedient Diels–Alder assembly of 4-aryl-4-phenylsulfonyl cyclohexanones

Alkylation, methylenation and highly regioselective Diels–Alder cycloaddition provided access to 4-aryl-4-phenylsulfonyl cyclohexanones, containing a quaternary sulfone-bearing carbon, in moderate to excellent overall yield for the three steps (38–78%). The efficient preparation of 4-aryl-4-phenylsu...

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Published inTetrahedron letters Vol. 45; no. 17; pp. 3345 - 3348
Main Authors Scott, Jeremy P., Hammond, Deborah C., Beck, Elizabeth M., Brands, Karel M.J., Davies, Antony J., Dolling, Ulf-H., Kennedy, Derek J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.04.2004
Elsevier
Subjects
Chemistry
Chemistry, Organic
Cycloadditions
Diels–Alder reactions
Methylenation
Physical Sciences
Science & Technology
Sulfones
Methylenation
Diels–Alder reactions
Cycloadditions
Sulfones
Diels-Alder reactions
cycloadditions
methylenation
sulfones
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Summary:Alkylation, methylenation and highly regioselective Diels–Alder cycloaddition provided access to 4-aryl-4-phenylsulfonyl cyclohexanones, containing a quaternary sulfone-bearing carbon, in moderate to excellent overall yield for the three steps (38–78%). The efficient preparation of 4-aryl-4-phenylsulfonyl cyclohexanones, containing a quaternary sulfone-bearing carbon centre, is described. Their synthesis proceeds in 38–78% overall yield by way of three steps: (i) sulfinate alkylation; (ii) methylenation; and (iii) regioselective Diels–Alder condensation with 2-trimethylsiloxybutadiene. The scope and limitations of the one-pot Mannich-type methylenation described were examined.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.03.031