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Molecules 2013, 18(2), 1626-1637; doi:10.3390/molecules18021626

Diastereoselective [2+2] Photocycloaddition of Chiral Cyclic Enones with Olefins in Aqueous Media Using Surfactants

1
Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan
2
Department of Applied Chemistry, Faculty of Engineering, Miyazaki University, 1-1 Gakuen Kibanadai-Nishi, Miyazaki 889-2155, Japan
*
Authors to whom correspondence should be addressed.
Received: 7 January 2013 / Revised: 15 January 2013 / Accepted: 21 January 2013 / Published: 28 January 2013
(This article belongs to the Special Issue New Trends in Photochemistry)
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Abstract

We conducted diastereodifferentiating [2+2] photocycloadditions of cyclo-hexenones modified with a chiral 8-(p-methoxy phenyl)menthyl auxiliary with olefins in water. Although the photoreaction didn’t proceed at all in pure water owing to very low solubility, the use of surfactants [sodium dodecyl sulfate (SDS) or dodecylamine hydrochloride (DAH)] and additive (organic solvent) enabled the reactions to progress with moderate to high conversions and yields. Furthermore, we synthesized a new menthol derivative substrate containing a (p-octyloxy)phenyl group for enhancing hydrophobicity, and elucidated that this new substrate was found to be a suitable chiral auxiliary in this asymmetric photoreaction in aqueous system. The additive effect of organic molecules on the yield and diastereoselectivity of the photo-adducts is also discussed.
Keywords: diastereoselectivity; [2+2] photocycloaddition; aqueous media; surfactant diastereoselectivity; [2+2] photocycloaddition; aqueous media; surfactant
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Nishiyama, Y.; Shibata, M.; Ishii, T.; Morimoto, T.; Tanimoto, H.; Tsutsumi, K.; Kakiuchi, K. Diastereoselective [2+2] Photocycloaddition of Chiral Cyclic Enones with Olefins in Aqueous Media Using Surfactants. Molecules 2013, 18, 1626-1637.

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