Diastereoselective Paternò-Büchi Reaction on Furan Derivatives-Reaction with Asymmetric Ketones

Title:Diastereoselective Paternò-Büchi Reaction on Furan Derivatives-Reaction with Asymmetric Ketones

Volume: 3 Issue: 5

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

Affiliation:

Keywords: diastereoselectivity, chiral ketone, 2+2 cycloaddition, Paterno-Buchi reaction

Abstract: The photochemical reaction of 1-phenyl-2-methyl-1-butanone with furan gave propiophenone via a Norrish Type II reaction. The same behavior was observed using 1-phenyl-2-methyl-1-pentanone. In this case, the product derived from a Norrish-Yang reaction was obtained. The photochemical reaction of 2- phenylpropiophenone with furan and 2-methylfuran gave the corresponding Paternò-Büchi adducts. 2- Methylfuran gave a mixture of regioisomers. All the products of the Paternò-Büchi reaction were obtained with > 98% de. The diastereoselectivity was explained by considering the relative stability of the biradical intermediates.

Cite this article as:

Pace Vita, Racioppi Rocco, Emanuele Lucia and D'Auria Maurizio, Diastereoselective Paternò-Büchi Reaction on Furan Derivatives-Reaction with Asymmetric Ketones, Letters in Organic Chemistry 2006; 3 (5) . https://dx.doi.org/10.2174/1570178610603050350