Sulfamic acid catalyzed oxonium-ene reactions under ball milling conditions: Straightforward access to highly functionalized Oxabicyclo[3.2.1]octenes

• Published in: Current research in green and sustainable chemistry Vol. 4; p. 100118
• Main Authors: Lambat, Trimurti L., Mahmood, Sami H., Taher, Deeb, Banerjee, Subhash
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 2021; Elsevier
• Subjects: Ball milling; Green procedure; Oxabicyclo[3.2.1]octenes; Recyclability; Solvent-free; Sulfamic acid; Ball milling; Oxabicyclo[3.2.1]octenes; Recyclability; Sulfamic acid; Solvent-free; Green procedure
• ISSN: 2666-0865; 2666-0865
• DOI: 10.1016/j.crgsc.2021.100118

Herein, we report a facile green procedure for the synthesis of oxabicyclo[3.2.1]octenes using sulfamic acid as catalyst under solvent-free ball milling conditions. A series of aldehydes or epoxides underwent oxonium-ene reaction with (−)-terpinen-4-ol under optimized conditions to produce a variety of oxabicyclo[3.2.1]octene derivatives. The excellent selectivity, higher isolated yields of the products, use of mild catalyst and solvent-free ball milling conditions, and recyclability are the major advantages of the present procedure. Herein, we report an proficient green procedure for the synthesis of oxabicyclo[3.2.1]octenes using sulfamic acid as catalyst under solvent-free ball milling conditions. The excellent selectivity, higher isolated yields of the products, use of mild catalyst and solvent-free ball milling conditions, recyclability are the major advantages of the present procedure. [Display omitted] •We propose a facile green procedure for the synthesis of oxabicyclo[3.2.1]octenes.•Sulfamic acid was used as catalyst under solvent-free ball milling conditions.•Eexcellent selectivity and higher isolated yields of the products were achieved.•The catalyst was recyclable for several subsequent reactions.