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

DOI: 10.4236/ijoc.2012.24045   PDF   HTML     2,634 Downloads   4,155 Views  


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.

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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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The authors declare no conflicts of interest.


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