Author(s)

Jun-ichi Yamaguchi, Kanako Nozaki Abe, Takayuki Suyama

Department of Applied Chemistry, Faculty of Engineering, Kanagawa Institute of Technology, Atsugi, Japan.

Diastereoselective conjugate addition of 1-enoyl-5-substituted hydantoins with allyltrimethylsilane in the presence of Ti(IV) chloride proceeded to give the corresponding allyl adducts in high yield and high diastereoselectivity. In order to determine the absolute configuration on the β-position of the acyl group, the hydantoin was removed by hydrolysis of the allyl adducts with a base to give the corresponding carboxylic acid. It was found that the absolute configuration was S on the basis of specific rotation.

Hydantoin; Conjugate Addition; Lewis Acid; Allyltrimethylsilane

J. Yamaguchi, K. Abe and T. Suyama, "Ti(IV) Chloride-Promoted Diastereoselective Conjugate Addition of 1-Enoyl-5-substituted Hydantoins with Allyltrimethylsilane," International Journal of Organic Chemistry, Vol. 2 No. 4, 2012, pp. 332-335. doi: 10.4236/ijoc.2012.24045.