ArticleBeilstein journal of organic chemistry2011
Chiral gold(I) vs chiral silver complexes as catalysts for the enantioselective synthesis of the second generation GSK-hepatitis C virus inhibitor.
Article in Beilstein journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed, 30 citations in OpenAlex.
- Recent advances of azomethine ylides for the synthesis of natural and synthetic bioactive pyrrolidines and spiropyrrolidines.RSC advances · 2026Review
- Application of 1,3-Dipolar Reactions between Azomethine Ylides and Alkenes to the Synthesis of Catalysts and Biologically Active Compounds.European journal of organic chemistry · 2018Review
- Gold(I)-catalyzed enantioselective cycloaddition reactions.Beilstein journal of organic chemistry · 2013Review
- Synthetic scope and DFT analysis of the chiral binap-gold(I) complex-catalyzed 1,3-dipolar cycloaddition of azlactones with alkenes.Beilstein journal of organic chemistry · 2013Article
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Authors and funding
5 authors at 2 institutions in 1 country.
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Abstract
The synthesis of a GSK 2(nd) generation inhibitor of the hepatitis C virus, by enantioselective 1,3-dipolar cycloaddition between a leucine derived iminoester and tert-butyl acrylate, was studied. The comparison between silver(I) and gold(I) catalysts in this reaction was established by working with chiral phosphoramidites or with chiral BINAP. The best reaction conditions were used for the total synthesis of the hepatitis C virus inhibitor by a four step procedure affording this product in 99% ee and in 63% overall yield. The origin of the enantioselectivity of the chiral gold(I) catalyst was justified according to DFT calculations, the stabilizing coulombic interaction between the nitrogen atom of the thiazole moiety and one of the gold atoms being crucial.
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