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Diastereoselective Intramolecular meta Photocycloaddition of Side-Chain-Substituted 5-(2-Methoxyphenyl)pent-1-enes

✍ Scribed by Johan L. Timmermans; Marc P. Wamelink; Gerrit Lodder; Jan Cornelisse

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
185 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

Irradiation of a series of 5-(2-methoxyphenyl)pent-1-enes interactions between the side-chain substituent and the ortho-methoxy group at the arene unit. Hydrogen bonding substituted with a hydroxy or trimethylsilyloxy group at the Ξ±-, Ξ²-, or Ξ³-position of the side-chain yields in all cases meta does not seem to be involved. The introduction of the sidechain substituents also influences the regioselectivity of the photocycloadducts, in which the configuration at the substituted carbon atom is mainly endo. This indicates that addition: The linear to angular adduct ratios are significantly increased compared to the case of the parent compound. the diastereoselectivity originates from minimization of steric (the benzylic position), the stereochemistry of this benzylic

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