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Diastereoselective Synthesis of Macrocyclic Spiro and Dispiro‐1,4‐dithianes, ‐1,4‐oxathianes, and ‐1,4‐dithiepanes through Intramolecular Sulfonium Ylides

Diastereoselective Synthesis of Macrocyclic Spiro and Dispiro‐1,4‐dithianes, ‐1,4‐oxathianes, and... The synthesis of functionalized C2‐symmetric as well as unsymmetrical macrocyclic spiro and dispiro‐1,4‐dithianes, ‐1,4‐oxathianes, and 1,4‐dithiepanes was achieved in a highly diastereoselective manner from the reactions of thiol‐protected cyclic and acyclic diazocarbonyl compounds in the presence of a rhodium(II) acetate dimer catalyst at room temperature. These macrocyclic compounds were obtained by the formation of 9‐ to 13‐membered intramolecular sulfonium ylides followed by a Stevens rearrangement. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Diastereoselective Synthesis of Macrocyclic Spiro and Dispiro‐1,4‐dithianes, ‐1,4‐oxathianes, and ‐1,4‐dithiepanes through Intramolecular Sulfonium Ylides

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References (48)

Publisher
Wiley
Copyright
© 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201500406
Publisher site
See Article on Publisher Site

Abstract

The synthesis of functionalized C2‐symmetric as well as unsymmetrical macrocyclic spiro and dispiro‐1,4‐dithianes, ‐1,4‐oxathianes, and 1,4‐dithiepanes was achieved in a highly diastereoselective manner from the reactions of thiol‐protected cyclic and acyclic diazocarbonyl compounds in the presence of a rhodium(II) acetate dimer catalyst at room temperature. These macrocyclic compounds were obtained by the formation of 9‐ to 13‐membered intramolecular sulfonium ylides followed by a Stevens rearrangement.

Journal

Asian Journal of Organic ChemistryWiley

Published: Jan 1, 2016

Keywords: ; ; ; ;

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