Rhodium Catalyzed [4 + 2 + 2] Cycloaddition and Alkyne Insertion: A New Route to Eight-Membered Rings
- 29 June 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (30) , 8784-8785
- https://doi.org/10.1021/ja026536x
Abstract
A novel variation of the rhodium catalyzed [4 + 2] reaction is reported. A catalyst system that forms an eight-membered ring product from the incorporation of an alkyne into a dienyne is discussed. The products are formed with high diastereoselectivity and in good yield. The highest yields are obtained with alkynes that possess either an oxygen or nitrogen in the propargyl position. Examples are presented where the tether between the alkyne and the diene contains three or four atoms.Keywords
This publication has 10 references indexed in Scilit:
- Serial [5+2]/[4+2] Cycloadditions: Facile, Preparative, Multi‐Component Syntheses of Polycyclic Compounds from Simple, Readily Available Starting MaterialsAngewandte Chemie International Edition in English, 2001
- The First Intermolecular Transition Metal-Catalyzed [5+2] Cycloadditions with Simple, Unactivated, VinylcyclopropanesJournal of the American Chemical Society, 2000
- Transition Metal-Catalyzed [6+2] Cycloadditions of 2-Vinylcyclobutanones and Alkenes: A New Reaction for the Synthesis of Eight-Membered RingsJournal of the American Chemical Society, 2000
- Asymmetric Total Synthesis of (+)-Aphanamol I Based on the Transition Metal Catalyzed [5 + 2] Cycloaddition of Allenes and VinylcyclopropanesOrganic Letters, 2000
- Rhodium(I)-Catalyzed Intramolecular Pauson−Khand ReactionOrganometallics, 1998
- Rhodium catalyzed intramolecular [4+2] cycloisomerization reactionsTetrahedron Letters, 1998
- On the Counterion Dependence of the Rhodium(I)-Catalysed [4 + 2] Cycloaddition - A Remarkable Accelerating Effect of the Hexafluoroantimonate AnionSynlett, 1998
- Transition Metal Catalyzed [5 + 2] Cycloadditions of Vinylcyclopropanes and Alkynes: A Homolog of the Diels-Alder Reaction for the Synthesis of Seven-Membered RingsJournal of the American Chemical Society, 1995
- On the asymmetric rh(I) catalyzed [4+2] cycloisomerization reaction. Electronic and torsional ligand control of absolute stereoselection.Tetrahedron, 1994
- Novel cyclization reactions on transition metal templates. The catalysis of intramolecular [4+2] cycloadditions by low-valent rhodium complexesJournal of the American Chemical Society, 1990