Diastereoselective [3+2]-photocycloaddition of chiral 1,4-naphthalenedicarboxylic esters to alkenes

Abstract [3+2]-Photocycloaddition of di-(−)-menthyl, di-(−)-8-phenylmenthyl, and di-(−)-bornyl 1,4-naphthalenedicarboxylates to alkenes, such as isobutene, styrene, and α-methylstyrene, proceeded with diastereoselectivity, up to 62% diastereomeric excess (de), largely depending on the concavity of the auxiliary, steric bulk of the substituents of the alkenes, and reaction temperature. The de values remarkably increased with decrease of the reaction temperature, and linear dependence of In(diastereomeric ratio) on 1/T was observed.