Abstract
A set of five chiral naphthalene derivatives 1 gave on photooxygenation the corresponding endoperoxides in excellent yields; the diastereoselectivity of singlet oxygen attack was determined and the directing effect of various carbon-containing substituents (CN, COOH, COOMe, CHO, CH 2OH) was rationalized in terms of attraction or repulsion in the transition state through electronic and steric effects.
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