Ring Modifications in Camphorimines Purely Organic or Promoted by Pt(II)

Abstract

The reactivity of 3-oxo-camphorsulfonylimine (1) was explored toward the formation of new organic species in processes strictly organic or catalyzed by platinum. Synthesis and characterization of (1S)-1-[7,7-dimethyl-2-(4-ethinylphenylimino)-3-oxo-bicyclo[2.2.1]heptanyl]-methanesulfonamide (2), (3aS,7R)-7-hydroxy-8,8-dimethyl-7-(N-methylamino-1-propynyl)-4,5,6,7-tetrahydro-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide (4a), (3aS,6aR,9aR)-8-benzyl-10,10-dimethyl-6a-hydroxy-9-(E-2-phenylethylidene)-3,3a,4,5,6,7-hexahydro-1H,9H-3a,6-methano-indeno[3a,4c]isothiazole 2,2-dioxide (6), and (2S, 3aS,6S)-9-benzyl-5,6-dihydro-11,11-dimethyl-10-phenylacetyl-3H-3a,6-methano-1H-yclonon[c]isothiazol-7(4H)-one 2-oxide (7) are reported as well as the activation of (1aS,3aS,7R)-7-hydroxy-1a,7-bis(3-phenyl-1-propynyl)-8,8-dimethyl-1,1a,4,5,6,7-hexahydro-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide (3a) toward ring annulation or ring expansion by reaction with Pt(II) depending on the reaction conditions.

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GRAPHICAL ABSTRACT

Keywords:

• Cascade processes
• catalysis
• platinum
• ring annulations
• ring expansion

ACKNOWLEDGMENTS

FCT-Fundação para a Ciência e Tecnologia (PEst-OE/QUI/UI0100/2011) and the NMR Network are greatfully acknowledged for financial support and facilities access, respectively.