| Abstract
| - The first example of a diastereoselective thio-Ugi reaction with chiral α-methylbenzylamine is described.The reaction results in formation of two diastereomers of thioamides, the major of which was isolated.We have found that under similar conditions stereochemical results of the thio-Ugi reaction are oppositeto stereochemical results of the Ugi reaction. Several chiral thioamides were synthesized. The reactionof thioamides with ammonia results in substituted amidines, which can be cyclized to imidazole derivativesin aqueous HCl. The synthesis of chiral imidazole derivatives was elaborated. Using certain approaches,both isomers of a key synthon in the synthesis of SB203386 (an orally bioactive HIV-1 protease inhibitor)were prepared. The scope, limitations, and stereochemistry of the approach are discussed.
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