The diastereoselectivity of the Paternò-Büchi reaction between 2,3-dihydrofuran and aromatic carbonyl compounds in organized medium

• Stereoselectivity of the photoreaction of benzaldehyde with 2,3-dihydrofuran is studied.
• Stereoselectivity increased when the reaction is performed within NaY zeolite.
• The substituent effect on benzaldehyde is studied.
• The interaction between HOMO and LUMO in the biradical accounts for the endo isomer.
• The exo isomer was obtained through an electron transfer process.

The Paternò-Büchi reaction between benzaldehyde and 2,3-dihydrofuran can be performed within the cavity of NaY zeolite. An increased stereoselectivity has been observed. When the reaction was performed with substituted benzaldehyde derivatives, different stereoselectivity has been observed. The stereoselectivity can be understood assuming an interaction in the biradical intermediate between the HSOMO and the LSOMO.

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