Stereoselectivity in the Paterno-Buchi Reaction on Chiral Allylic Alcohols, for A Discussion of the Hydroxy Directing Effect

Title: Stereoselectivity in the Paterno-Buchi Reaction on Chiral Allylic Alcohols, for A Discussion of the Hydroxy Directing Effect

Volume: 2 Issue: 2

Author(s): Maurizio D'Auria, Lucia Emanuele and Rocco Racioppi

Affiliation:

Keywords: cycloaddition, allylic alcohols, stereoselectivity, paternò-büchi reaction, photochemistry, hydroxy directing effect

Abstract: The stereoselectivity of the photochemical reaction between acetophenone and 2,2,5-trimethyl-4- hexen-3-ol was explained on the basis of a DFT study. Conformational analysis of the starting material showed that two conformations were the most stable ones. Assuming that the attack of the excited carbonyl group occurred on the same side of the hydroxy group (due to hydrogen bond or to the formation of a complex), the possible conformations of the biradical intermediate was examined. Only the precursors of the threo stereoisomer was obtained in agreement with experimental results.

Cite this article as:

D'Auria Maurizio, Emanuele Lucia and Racioppi Rocco, Stereoselectivity in the Paterno-Buchi Reaction on Chiral Allylic Alcohols, for A Discussion of the Hydroxy Directing Effect, Letters in Organic Chemistry 2005; 2 (2) . https://dx.doi.org/10.2174/1570178053202892