Determination of the absolute configuration of two α v β 6 integrin inhibitors for the treatment of idiopathic pulmonary fibrosis and investigations on the asymmetric 1,4-addition of arylboronic acids to crotonate esters bearing a C4-oxygen substituent
| Autor: | Panayiotis A. Procopiou, Royston C. B. Copley, Tim N. Barrett, Christopher J. Tame |
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| Rok vydání: | 2017 |
| Předmět: |
Tetrafluoroborate
010405 organic chemistry Stereochemistry Norbornadiene Organic Chemistry Enantioselective synthesis Substituent Absolute configuration chemistry.chemical_element 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Rhodium Inorganic Chemistry chemistry.chemical_compound chemistry Physical and Theoretical Chemistry Butenolide |
| Zdroj: | Tetrahedron: Asymmetry. 28:1384-1393 |
| ISSN: | 0957-4166 |
| Popis: | The absolute configuration of two novel αvβ6 integrin inhibitors was established via degradation to the corresponding C3-aryl substituted butyrolactone. The configuration of the resulting lactones was established by asymmetric synthesis using 1,4-addition of arylboronic acids to butenolide, catalysed by bis(norbornadiene)rhodium (I) tetrafluoroborate in the presence of (R)-BINAP, and confirmed by X-ray crystallography. Studies on arylboronic acid conjugate additions to acyclic crotonate esters bearing a γ-oxygen substituent are also reported. Three Rh catalysts were investigated and the one giving the highest enantioselectivity was bis(norbornadiene)rhodium (I) tetrafluoroborate. |
| Databáze: | OpenAIRE |
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