This research was partly supported by a Grant-in-Aid for Scientific Research on Priority Areas (No. 19028015, Chemistry of Concerto Catalysis) from the Ministry of Education, Culture, Sports, Science and Technology (Japan). We thank Yusuke Aida (TUAT) for his experimental assistance and Takasago International Corporation for the gift of modified binap ligands. H8-binap=2,2′-bis(diphenylphosphanyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl.
Highly Regio-, Diastereo-, and Enantioselective [2+2+2] Cycloaddition of 1,6-Enynes with Electron-Deficient Ketones Catalyzed by a Cationic RhI/H8-binap Complex†
Article first published online: 8 JAN 2008
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 47, Issue 7, pages 1312–1316, February 1, 2008
How to Cite
Tanaka, K., Otake, Y., Sagae, H., Noguchi, K. and Hirano, M. (2008), Highly Regio-, Diastereo-, and Enantioselective [2+2+2] Cycloaddition of 1,6-Enynes with Electron-Deficient Ketones Catalyzed by a Cationic RhI/H8-binap Complex. Angew. Chem. Int. Ed., 47: 1312–1316. doi: 10.1002/anie.200704758
- Issue published online: 25 JAN 2008
- Article first published online: 8 JAN 2008
- Manuscript Received: 15 OCT 2007
- Grant-in-Aid for Scientific Research on Priority Areas. Grant Number: 19028015
- asymmetric catalysis;
Two quaternary carbon centers are created in the title reaction to form fused dihydropyrans (see scheme). The same catalyst promotes the ortho functionalization of aryl ketones with 1,6-enynes with excellent regio- and enantioselectivity. Z=amide, C(CO2Me)2, O; E=CO2Et, Ac; R1=Me, aryl, CO2Me; R2=Me; R3=Me, CO2Et.