Substituent Effects in the Diastereoselective (4 + 2) Cycloaddition of Chiral Naphthalene Derivatives with Singlet Oxygen.

Abstract From 1-bromo-4-methylnaphthalene eight chiral derivatives 1 with a variety of functional groups at the stereogenic center were prepared, which with singlet oxygen led to the corresponding endoperoxides 2 in substituent-dependent π-facial selectivity of stereoelectronic origin.