Next Article in Journal
Use of Pyrogallol Red and Pyranine as Probes to Evaluate Antioxidant Capacities towards Hypochlorite
Next Article in Special Issue
Singlet Oxygen in Antimicrobial Photodynamic Therapy: Photosensitizer-Dependent Production and Decay in E. coli
Previous Article in Journal
Microwave-Assisted Improved Synthesis of Pyrrolo[2,3,4-kl]acridine and Dihydropyrrolo[2,3,4-kl]acridine Derivatives Catalyzed by Silica Sulfuric Acid
Previous Article in Special Issue
Photochemical Synthesis and Properties of 1,6- and 1,8-Naphthalenophanes
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

1
,
1
,
1
,
1
,
1
,
2,*  and 1,*
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)
Download PDF [269 KB, uploaded 18 June 2014]   |  

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 (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert