E- and chemoselective thia-Michael addition to benzyl allenoate

Abstract

Different thiols were successfully reacted with benzyl allenoate resulting in E-selective thia-Michael addition product with α,β-unsaturation as confirmed by single crystal x-ray crystallographic analysis. The thia-Michael addition is chemoselective and free amine and alcohol groups were well tolerated. Catalytic triethylamine was required for high conversion. Fair to excellent yields were obtained for a variety of aliphatic, aryl and heteroaryl thiols.

Graphical Abstract

Keywords:

• Thia-Michael addition
• α-β-unsaturation
• E-selective
• β-substituted thioenoates
• chemoselective

5. Supplementary data

See the attached supporting information file with detailed experimental procedures and spectra for all compounds. The single crystal X-ray data associated with this article can be found at CCDC repository numbers, 1560208 and 1560209.

Disclosure statement

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

Additional information

Funding

We are grateful to Higher Education Commission (HEC), Pakistan for the financial support under the NRPU program (Project No. 20-3069/NRPU.R&D/13) and Start up Research Grant (Project No. PM-IPFP-HRD-HEC-2011-402). Rifhat Bibi is thankful to HEC for Indigenous Ph. D. Fellowship.