Diastereoselective photocycloaddition reactions of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furans governed by chiral auxiliaries and hydrogen bonding interactions

作者：Maeda Hajime^*; Koshio Norihiro; Tachibana Yuko; Chiyonobu Kazuhiko; Konishi Gen ichi; Mizuno Kazuhiko^*

来源：Journal of Photochemistry and Photobiology A: Chemistry , 2017, 349: 7-17.

DOI：10.1016/j.jphotochem.2017.08.052

• Photoreaction
• Photocycloaddition
• Diastereoselectivity
• Chiral auxiliary
• Hydrogen bonding

By using chiral auxiliaries and hydrogen bonding interactions, we have developed diastereoselective photocycloaddition of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furan derivatives. In photoreactions of (l)-menthyl 2-naphthalenecarboxylate with furan and 3-furanmethanol, respective maximum 48% and 40% diastereomeric excesses (d.e.) are observed. In photoreactions of di-8-phenyl-(l)-menthyl 2,3-naphthalenedicarboxylate with 3-furanmethanol, maximum 67% d.e. is obtained. Use of solvents of low polarity, low temperatures and low furan concentration leads to increased diastereoselectivities. Variable-temperature (VT) NMR and fluorescence quenching studies indicate that hydrogen bonding interactions between the carbonyl oxygen of naphthalenecarboxylic acid esters and the OH group in 3-furantnethanol take place in both the ground and excited states. The results of computational studies show that geometries of C-2 symmetric naphthalenedicarboxylate reactants are important in governing the high diastereoselectivity in the photoreactions of 2,3-naphthalenedicarboxylates.

• 出版日期2017-12-1