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Ti(IV) Chloride-Promoted Diastereoselective Conjugate Addition of 1-Enoyl-5-substituted Hydantoins with Allyltrimethylsilane

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DOI: 10.4236/ijoc.2012.24045    2,508 Downloads   4,033 Views  

ABSTRACT

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.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

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.

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