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

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
45
Issue
17
Identifiers
DOI: 10.1016/j.tetlet.2004.03.031
Keywords
  • Cycloadditions
  • Diels–Alder Reactions
  • Methylenation
  • Sulfones

Abstract

Abstract 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.

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