Vinyl Dihydropyrans and Dihydrooxazines: Cyclizations of Catalytic Ruthenium Carbenes Derived from Alkynals and Alkynones
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ISSN: 1433-7851
E-ISSN: 1521-3773
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Abstract
A novel synthesis of 2‐vinyldihydropyrans and dihydro‐1,4‐oxazines (morpholine derivatives) from alkynals and alkynones has been developed. The cyclizations require a mild generation of catalytic ruthenium carbenes from terminal alkynes and (trimethylsilyl)diazomethane followed by trapping with carbonyl nucleophiles. Mechanistic aspects of the new cyclizations are discussed.
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NOTICE: This is the peer reviewed version of the following article: Cambeiro, F., López, S., Varela, J. A., Saá, C. (2014). Vinyl Dihydropyrans and Dihydrooxazines: Cyclizations of Catalytic Ruthenium Carbenes Derived from Alkynals and Alkynones. Angew. Chem. Int. Ed., 53, 23, 5959-5963. [doi: 10.1002/anie.201400675]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for self-archiving
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Cambeiro, F., López, S., Varela, J. A., Saá, C. (2014). Vinyl Dihydropyrans and Dihydrooxazines: Cyclizations of Catalytic Ruthenium Carbenes Derived from Alkynals and Alkynones. Angew. Chem. Int. Ed., 53, 23, 5959-5963
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https://doi.org/10.1002/anie.201400675Sponsors
This work was supported by MICINN (Spain) [projects CTQ2011-28258, Consolider Ingenio 2010 (CSD2007-0006)] and Xunta de Galicia and the European Regional Development Fund (project CN2011/054 and EM 2012/051). F.C. thanks XUGA for a predoctoral contract
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© 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for self-archiving