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

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

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Received: 7 January 2013; in revised form: 15 January 2013 / Accepted: 21 January 2013 / Published: 28 January 2013
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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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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(2):1626-1637.

Chicago/Turabian Style

Nishiyama, Yasuhiro; Shibata, Mikiko; Ishii, Takuya; Morimoto, Tsumoru; Tanimoto, Hiroki; Tsutsumi, Ken; Kakiuchi, Kiyomi. 2013. "Diastereoselective [2+2] Photocycloaddition of Chiral Cyclic Enones with Olefins in Aqueous Media Using Surfactants." Molecules 18, no. 2: 1626-1637.



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