A direct synthetic route to allyl sulfides from cyclic Morita–Baylis–Hillman alcohols

ABSTRACT

p-TsOH-mediated the direct α-substitution of cyclic Morita–Baylis–Hillman alcohols with aliphatic and aromatic thiols in refluxing THF. The reaction proceeded with complete α-regioselectivity and provided the corresponding allyl sulfides in moderate to good yields.

GRAPHICAL ABSTRACT

KEYWORDS:

• Allyl sulfide
• regioselectivity
• Morita–Baylis–Hillman
• Brønsted acid
• allylic substitution

Disclosure statement

No potential conflict of interest was reported by the authors.

Notes

1. The separation of diastereomers could not be achieved by column chromatography, and on the basis of their 1H NMR spectrum, the diastereomeric ratio could not be determined.

Additional information

Funding

We gratefully acknowledge financial support of this work by the Ministry of Higher Education of Tunisia. The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding of this research through the Research Group Project No RGP-243.