ChemInform Abstract: A 2‐Pyrone Cycloaddition Route to Functionalized Aromatic Boronic Esters.

Abstract

A 2-Pyrone Cycloaddition Route to Functionalized Aromatic Boronic Esters. -A range of electron-deficient 2-pyrones undergoes with alkynylboronates a [4 + 2] cycloaddition/retro-cycloaddition reaction to give the aromatic boronic esters with good to excellent levels of regiocontrol in many cases. The regioselectivity varies according to the position of the electron-withdrawing groups on the pyrone and could be therefore controlled by the appropriate positioning of these groups. -(DELANEY, P. M.; BROWNE, D. L.; ADAMS, H.; PLANT, A.; HARRITY*, J. P. A.; Tetrahedron 64 (2008) 5, 866-873; Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK; Eng.) -Klein 24-164

Synthesis and Applications of Group 14-metalated Arylboranes

“…64, 67-69 via [4+2] cycloaddition with reactive cyclic dienes such as substituted cyclopentadienone 63 (Scheme 26) and 2-pyrone derivatives 65-66 (Scheme 27)[36][37][38].…”