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

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Author(s): Jun-ichi Yamaguchi | Kanako Nozaki Abe | Takayuki Suyama

Journal: International Journal of Organic Chemistry
ISSN 2161-4687

Volume: 02;
Issue: 04;
Start page: 332;
Date: 2012;
Original page

Keywords: Hydantoin | Conjugate Addition | Lewis Acid | Allyltrimethylsilane

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.
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