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

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

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 5 , 2006

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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.

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

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Article Details

Year: 2006
Page: [350 - 355]
Pages: 6
DOI: 10.2174/1570178610603050350
Price: $65

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