Organic reaction in water. Part 31: diastereoselectivity in Michael additions of thiophenol to nitro olefins in aqueous media

Abstract

Thiophenol reacts with nitro olefins in aqueous media to give the corresponding nitro-sulfides in 58-95% yield. This procedure results in selective formation of the anti products. In the case of the cyclic nitro olefin 1-nitro-cyclohexene the only product observed was the cis-1-nitro-2-(phenylthio)cyclohexane. This methodology is of interest due to the use of water as solvent, thus minimizing the cost, the operational hazards and environmental pollution.

Keywords

• Michael additions in water
• nitro olefins
• thio compounds