[2+2] Photocycloaddition of Symmetrically Disubstituted Alkenes to 2(5H)‐Furanones: Diastereoselective Entry to 1,2,3,4‐Tetrasubstituted Cyclobutanes

Abstract

A study on the [2+2] photochemical cycloaddition of 1,4-difunctionalized 2-butenes to 2(5H)-furanones is presented. These reactions deliver 1,2,3,4-tetrasubstituted cyclobutanes with suitable functionalization in the four side chains for further synthetic elaboration. The effects of the substituents in both the lactone and the 2-butene on the stereoselectivity

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

“…The facial diastereoselectivity in intermolecular [2 + 2] photocycloaddition reactions of 2­(5 H )-furanones is variable and depends on the nature of the substituent in the 5-position and on the olefinic component . In the last two decades, Alibés, Figueredo, Font, and co-workers widely employed free and oxygen-protected 5-hydroxymethyl-2­(5 H )-furanones. − Significant diastereoselectivities were recorded in several intermolecular [2 + 2] photocycloaddition reactions, and numerous applications were disclosed for the enantioselective synthesis of terpenoid natural products − and new nucleoside analogues (Scheme ). − …”

Synthesis of 3‐Azabicyclo[3.2.0]heptane Derivatives as γ‐Aminobutyric Acid Analogues through Intermolecular [2+2] Photo­cycloaddition

“…For the construction of such compounds exhibiting a hydroxymethyl or methoxymethyl group, lactone rac-13 was considered a suitable starting compound (Scheme 3). [33,34] Although the desired cycloaddition product rac-13 was formed, the reaction did not go to completion, even on extension of the irradiation time. [31,32] Nevertheless, it seemed worthwhile to attempt the construction of rac-13 by an intermolecular [2+2] photocycloaddition reaction of 12 with N-trifluoroactyl-3-pyrroline (6) because this appeared to provide the most direct access to this compound.…”

Design, synthesis, molecular docking study and toxicological evaluation potential of new spiro and fused heterocycles against agricultural insect pests

“…Spiro compound 14 has unique non-planar structures and great potential for binding to biomolecules (HGP) because of their inherent rigid chiral structure. Molecular docking computational study is considered as a robust tool for the detection of the potential larvicidal activity of many previously reported structures [52].…”