Asymmetric intramolecular pauson-khand reaction mediated by a remote sulfenyl or sulfinyl group |
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Authors: | José Luis García Ruano Esther Torrente Alejandro Parra José Alemán Ana M Martín-Castro |
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Institution: | Departamento de Química Orgánica (Módulo 01), Facultad de Ciencias, Universidad Autónoma de Madrid , Cantoblanco 28049 Madrid, Spain. |
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Abstract: | In this work, we report the use of the asymmetric intramolecular Pauson-Khand reactions of 4-aryl-4-cyano-1,6-enynes for obtaining enantiomerically enriched bicyclo3.3.0]octenones, and the influence of both the quaternary stereocenter and the sulfur functions located at ortho-position of the aryl group, on their stereoselectivity and reactivity. The sulfenyl derivatives bearing substituted or unsubstituted triple bonds and mono- and disubstituted alkene moieties afford bicyclo3.3.0]octenones in high yields with complete diastereocontrol. These results are explained by assuming the association of the lone electron pair at sulfur to the Co-alkyne complexes. |
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