Chirality transfer in the synthesis of 2,3-dihydro-1,4-dithiine derivatives

Abstract

A new method for the synthesis of chiral 2,3-dihydro-1,4-dithiine derivatives that involves a reaction of chiral cyclic aliphatic dithioacetal in the presence of Lewis acid has been developed. The title product contains a 1,4-dithiane substituent with two stereogenic centers. The presence of a stereogenic center in the α position to the cyclic dithioacetal substrate controls the stereogenicity of two centers in the newly formed molecule whose absolute configuration is defined. The mechanism based on chirality transfer process was proposed.

Graphical Abstract

Keywords:

• Chirality transfer
• cyclic aliphatic dithioacetal
• 2,3-dihydro-1,4-dithiine
• Lewis acid

Acknowledgments

NMR spectra were recorded in the Laboratory of Spectrometry, Faculty of Chemistry, Rzeszow University of Technology.

Disclosure statement

No conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by the Polish Ministry of Science and Higher Education [grant DS.CM.20001]; financial support of the vice-Rector for RUT education is greatly appreciated; X-ray diffraction study was financed by Warsaw University of Technology.