Abstract
AbstractThe diastereoselective [2+2] photocycloaddition of cyclohexenonecarboxylates containing various chiral auxiliaries to ethylene is described. The effect of the auxiliary, reaction temperature, and solvent on diastereoselectivity was examined. The (−)‐8‐(p‐methoxyphenyl)menthyl group was found to be the most effective chiral auxiliary. The photoreaction of (−)‐8‐(p‐methoxyphenyl)menthyl cyclohexenonecarboxylate in methylcyclohexane at −78°C gave the corresponding bicyclo[4.2.0]octanone derivative in 81% diastereomeric excess (d.e.). The extent of diastereoselectivity was found to be closely related to the most stable π‐stack conformation of the starting cyclohexenones. Chirality 15:504–509, 2003. © 2003 Wiley‐Liss, Inc.
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