Cyclic sulfones from double conjugate addition of Rongalite

Abstract

Cyclic sulfones are obtained in up to 92% yield by double conjugate addition of Rongalite (sodium hydroxymethyl sulfinate) to dienones. The major product in each case is the kinetic trans-isomer of the 3,5-disubstituted ketosulfone. Eleven examples, including aryl and alkyl substituted substrates, are reported. The advantages of the method are its experimental simplicity, tolerance for both protic and oxidation-sensitive functional groups, and sterically challenging substrates. The work also significantly expands the scope of Rongalite as a conjugate nucleophile.

Graphical Abstract

Keywords:

• Conjugate addition
• dienones
• Rongalite
• sulfones

Acknowledgments

S. Finn and R. Murtada (Montclair State) are acknowledged for mass spectra as are Dr N. Dayal and Prof. H. Sintim (Purdue University).

Additional information

Funding

We thank Montclair State University for startup funds, the NSF for an MRI grant (# 2116596, PI Dr. J. Gao, Montclair State University), and the ACS Petroleum Research Fund for additional financial support (Grant #65204-UR1).