diastereoselective [2+2] photocycloaddition of chiral cyclic enones with olefins in aqueous media using surfactants
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ID: 194057
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.
| Reference Key |
nishiyama2013moleculesdiastereoselective
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| Authors | ;Yasuhiro Nishiyama;Mikiko Shibata;Takuya Ishii;Tsumoru Morimoto;Hiroki Tanimoto;Ken Tsutsumi;Kiyomi Kakiuchi |
| Journal | Journal of ethnopharmacology |
| Year | 2013 |
| DOI |
10.3390/molecules18021626
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