Stereoselective addition of 2-phenyloxazol-4-yl trifluoromethanesulfonate to N-sulfinyl imines: application to the synthesis of the HCV protease inhibitor boceprevir.

doi:10.1021/jo301856f

Paper

Stereoselective addition of 2-phenyloxazol-4-yl trifluoromethanesulfonate to N-sulfinyl imines: application to the synthesis of the HCV protease inhibitor boceprevir.

Published Jan 18, 2013 · W. Morris, K. Muppalla, C. Cowden

The Journal of organic chemistry

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5

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Abstract

The stereoselective addition of 2-phenyloxazol-4-yl trifluoromethanesulfonate to N-sulfinylimines is described. Vinyl anions derived from enol triflate 2 undergo 1,2-addition with a variety of aldimines to afford the corresponding secondary sulfonamides as single diastereomers. The absolute stereochemistry was confirmed by X-ray crystallography which provides support that the reaction proceeds through an open, nonchelate transition state. This methodology has been applied to the synthesis of the ketoamide fragment of the protease inhibitor boceprevir.

Study Snapshot

The stereoselective addition of 2-phenyloxazol-4-yl trifluoromethanesulfonate to N-sulfinylimines allows for the synthesis of the HCV protease inhibitor boceprevir.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Stereoselective addition of 2-phenyloxazol-4-yl trifluoromethanesulfonate to N-sulfinyl imines: application to the synthesis of the HCV protease inhibitor boceprevir.

References

Protease inhibitors for the treatment of chronic hepatitis C genotype-1 infection: the new standard of care.

Protease inhibitors, such as boceprevir and telaprevir, have improved response rates for chronic hepatitis C genotype-1 infection, but may have side effects, high costs, and drug interactions.

New Pharmacotherapy for Hepatitis C

New pharmacotherapy, including oral protease inhibitors boceprevir and telaprevir, significantly improves viral eradication rates and shows promise for future treatments.

Asymmetric vinylogous Mannich reactions: a versatile approach to functionalized heterocycles.

Asymmetric vinylogous Mannich reactions provide a versatile approach to functionalized heterocycles, yielding 5-aminoalkylbutenolides with potential applications in bioactive compound synthesis.

Large-scale asymmetric synthesis of the bioprotective agent JP4-039 and analogs.

This study developed a scalable one-pot method for asymmetric synthesis of bioprotective agent JP4-039 and its analogs, enabling efficient and versatile bioprotective agent production.

Synthesis and applications of tert-butanesulfinamide.

Tert-butanesulfinamide is a versatile and useful reagent for synthesis of various -amino acid derivatives, including -amino amides, -amino amides, and -amino phosphonates.

Citations