Stereoselective Inter- and Intramolecular Pauson–Khand Reactions ofN-(2-Alkynoyl) Derivatives of Chiral Oxazolidin-2-ones
1999; Wiley; Volume: 1999; Issue: 12 Linguagem: Inglês
10.1002/(sici)1099-0690(199912)1999
ISSN1434-193X
AutoresSı́lvia Fonquerna, Ramón Rios, Albert Moyano, Miquel À. Pericàs, Antoni Riéra,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoEuropean Journal of Organic ChemistryVolume 1999, Issue 12 p. 3459-3478 Full PaperFull Access Stereoselective Inter- and Intramolecular Pauson–Khand Reactions of N-(2-Alkynoyl) Derivatives of Chiral Oxazolidin-2-ones Sílvia Fonquerna, Sílvia Fonquerna Unitat de Recerca en Síntesi Asimètrica, Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, c/Martí i Franquès, 1–11, E-08028-Barcelona, Spain Fax: (internat.) + 34-93/339-7878Search for more papers by this authorRamon Rios, Ramon Rios Unitat de Recerca en Síntesi Asimètrica, Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, c/Martí i Franquès, 1–11, E-08028-Barcelona, Spain Fax: (internat.) + 34-93/339-7878Search for more papers by this authorAlbert Moyano, Albert Moyano [email protected] Search for more papers by this authorMiquel A. Pericàs, Miquel A. PericàsSearch for more papers by this authorAntoni Riera, Antoni Riera Unitat de Recerca en Síntesi Asimètrica, Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, c/Martí i Franquès, 1–11, E-08028-Barcelona, Spain Fax: (internat.) + 34-93/339-7878Search for more papers by this author Sílvia Fonquerna, Sílvia Fonquerna Unitat de Recerca en Síntesi Asimètrica, Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, c/Martí i Franquès, 1–11, E-08028-Barcelona, Spain Fax: (internat.) + 34-93/339-7878Search for more papers by this authorRamon Rios, Ramon Rios Unitat de Recerca en Síntesi Asimètrica, Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, c/Martí i Franquès, 1–11, E-08028-Barcelona, Spain Fax: (internat.) + 34-93/339-7878Search for more papers by this authorAlbert Moyano, Albert Moyano [email protected] Search for more papers by this authorMiquel A. Pericàs, Miquel A. PericàsSearch for more papers by this authorAntoni Riera, Antoni Riera Unitat de Recerca en Síntesi Asimètrica, Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, c/Martí i Franquès, 1–11, E-08028-Barcelona, Spain Fax: (internat.) + 34-93/339-7878Search for more papers by this author First published: 15 November 1999 https://doi.org/10.1002/(SICI)1099-0690(199912)1999:12 3.0.CO;2-LCitations: 20AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract A complete account of the intermolecular and intramolecular Pauson–Khand reactions of N-(2-alkynoyl) derivatives of chiral 2-oxazolidinones is presented. The intermolecular Pauson–Khand reactions with norbornene or norbornadiene take place under mild conditions and in high yields. Phenyl- or trimethylsilylpropiolate derivatives lead to the exclusive formation of 1,4-dicarbonyl regioisomers, while mixtures of 1,3- and 1,4-regioisomers are obtained with tetrolate derivatives. The diastereoselectivity of the reaction, determined by the substitution pattern of the oxazolidinone moieties, can be very high (up to 17.5:1 dr) for the formation of 1,4-dicarbonyl regioisomers, and the diastereomeric products can often be separated by column chromatography. Under the appropriate conditions, the intramolecular Pauson–Khand reactions of oxazolidinone-derived enynes can also take place with very good yields, but with low diastereoselectivities. The absolute configurations of several adducts have been determined, and the stereochemical outcome of the reaction has been rationalized. References 1 Reviews on the Pauson–Khand reaction: [1a] P. L. Pauson, I. U. Khand, Ann. N. Y. Acad. Sci. 1977 295, 2–14. 10.1111/j.1749-6632.1977.tb41819.x CASGoogle Scholar[1b] – P. L. Pauson, Tetrahedron 1985 41, 5855–5860. 10.1016/S0040-4020(01)91424-3 CASWeb of Science®Google Scholar[1c] – N. E. Schore, Org. React. 1991 40, 1–90. CASGoogle Scholar[1d] – N. E. Schore, in Comprehensive Organic Synthesis (Ed.: B. M. Trost), Pergamon Press, Oxford, 1991 vol. 5, pp. 1037–1064. 10.1016/B978-0-08-052349-1.00145-1 Google Scholar[1e] – N. E. Schore, in Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. Stone, G. 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