Diastereoselective Intramolecular Photochemical [2+2] Cycloaddition Reactions of Tethered L-(+)-Valinol Derived Tetrahydrophthalimides

Abstract

Intramolecular photochemical [2 + 2] cycloaddition of allyl alcohol linked to amino acid derived 3,4,5,6-tetrahydrophthalimides, either via a carbonate or silicon tether, gives the corresponding cyclobutanes in excellent yield with diastereoselectivities as high as 8:1.