Journal
TETRAHEDRON
Volume 66, Issue 46, Pages 9032-9040Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.09.009
Keywords
[2+2+2] Cycloaddition; Rhodium; Sulfinamide ligands; Alkynes; Enediynes
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Funding
- Spanish MICINN [CTQ2008-05409, CTQ2008-00763]
- IRB Barcelona
- Generalitat de Catalunya [2009SGR637, 2009SGR00901]
- AGAUR
- University of Girona (UdG)
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The combination of cationic rhodium(I) complexes with N-phosphino tert-butylsulfinamides (PNSO) ligands is efficient for catalytic intra- and intermolecular [2+2+2] cycloaddition reactions. PNSO ligands are a new class of chiral bidentate ligands, which have the characteristic of combining the easily accessible sulfur chirality with the coordinating capacity of phosphorous. Cycloaddition of open-chained and macrocyclic E-enediynes with these chiral complexes have proved to be highly efficient in terms of yields, giving moderate enantiomeric excesses of the corresponding cyclohexadiene derivatives. In addition Rh(I)/PNSO complexes catalyzed the intermolecular cycloaddition of diynes with monoalkynes in mild reaction conditions and short reaction times. (C) 2010 Elsevier Ltd. All rights reserved.
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