%0 Journal Article
%T Diastereoselective [2+2] Photocycloaddition of Chiral Cyclic Enones with Olefins in Aqueous Media Using Surfactants
%A Yasuhiro Nishiyama
%A Mikiko Shibata
%A Takuya Ishii
%A Tsumoru Morimoto
%A Hiroki Tanimoto
%A Ken Tsutsumi
%A Kiyomi Kakiuchi
%J Molecules
%D 2013
%I MDPI AG
%R 10.3390/molecules18021626
%X 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.
%K diastereoselectivity
%K [2+2] photocycloaddition
%K aqueous media
%K surfactant
%U http://www.mdpi.com/1420-3049/18/2/1626