Abstract
Mechanistic studies on silylformylation have led to the discovery of a series of new carbocyclizations involving alkynes and hydrosilanes. Cyclohydrocarbonylation processes have been devised by combining hydroformylation and cyclization. These new reactions serve as powerful methods for the rapid construction of monocyclic, bicyclic, and fused ring systems from readily obtainable starting materials.
Similar content being viewed by others
References
C. Botteghi, S. Paganelli, A. Schionato and M. Marchetti, Chirality 3 (1991) 355.
B. Breit and W. Seiche, Synthesis (2001) 1.
P. Eilbracht, L. Bärfacker, C. Buss, C. Hollmann, B.E. Kitsos-Rzychon, C.L. Kranemann, T. Rische, R. Roggenbuck and A. Schmidt, Chem. Rev. 99 (1999) 3329.
I. Ojima, M. Tzamarioudaki, Z.Y. Li and R.J. Donovan, Chem. Rev. 96 (1996) 635.
I. Matsuda, A. Ogiso, S. Sato and Y. Izumi, J. Am. Chem. Soc. 111 (1989) 2332.
I. Ojima, R.J. Donovan and N. Clos, Organometallics 10 (1991) 2606.
I. Ojima, R.J. Donovan, M. Eguchi, W.R. Shay, P. Ingallina, A. Korda and Q.P. Zeng, Tetrahedron 49 (1993) 5431.
F. Monteil, I. Matsuda and H. Alper, J. Am. Chem. Soc. 117 (1995) 4419.
I. Ojima, E. Vidal, M. Tzamarioudaki and I. Matsuda, J. Am. Chem. Soc. 117 (1995) 6797.
I. Ojima and E.S. Vidal, Organometallics 18 (1999) 5103.
D. Bonafoux, S.Y. Lee, C.H. Jiang and I. Ojima, in: 219th Am. Chem. Soc. National Meeting, Abstracts (2000) ORGN598.
C. Jiang, S.Y. Lee and I. Ojima, in: 217th Am. Chem. Soc. National Meeting, Abstracts (1999) ORGN257.
J.L. Leighton and E. Chapman, J. Am. Chem. Soc. 119 (1997) 12416.
D. Bonafoux and I. Ojima, Organic Lett. 3 (2001) 1303.
D. Bonafoux, H. Hara, A.C. Moralee and I. Ojima, in: 222nd Am. Chem. Soc. National Meeting, Abstracts (2001) ORGN000.
I. Matsuda, A. Ogiso and S. Sato, J. Am. Chem. Soc. 112 (1990) 6120.
I. Matsuda, J. Sakakibara and H. Nagashima, Tetrahedron Lett. 32 (1991). 7431.
I. Ojima, D. Machnik, R.J. Donovan and O. Mneimne, Inorg. Chim. Acta 251 (1996) 299.
I. Ojima, R.J. Donovan and W.R. Shay, J. Am. Chem. Soc. 114 (1992) 6580.
S.Y. Lee, Ph.D. thesis, State University of New York at Stony Brook (2000).
A.T. Vu, J.V. McCullagh, S.Y. Lee and I. Ojima, in: 217th Am. Chem. Soc. National Meeting, Abstracts 217 (1999) ORGN520.
Y. Fukuta, I. Matsuda and K. Itoh, Tetrahedron Lett. 40 (1999) 4703.
I. Ojima, D.A. Fracchiolla, R.J. Donovan and P. Banerji, J. Org. Chem. 59 (1994) 7594.
I. Ojima, D.F. Kass and J.W. Zhu, Organometallics 15 (1996) 5191.
I. Ojima, J.W. Zhu, E.S. Vidal and D.F. Kass, J. Am. Chem. Soc. 120 (1998) 6690.
P.L. Pauson, Tetrahedron 41 (1985) 5855.
N.E. Schore, Chem. Rev. 88 (1988) 1081.
H.J. Knölker and J. Heber, Synlett (1993) 924.
A.J. Pearson and A. Perosa, Organometallics 14 (1995) 5178.
I. Ojima, J.V. McCullagh and W.R. Shay, J. Organomet. Chem. 521 (1996) 421.
I. Ojima, A.T. Vu, J.V. McCullagh and A. Kinoshita, J. Am. Chem. Soc. 121 (1999) 3230.
I. Ojima, N. Clos, R.L. Donovan and P. Ingallina, Organometallics 9 (1990) 3127.
R.S. Tanke and R.H. Crabtree, J. Am. Chem. Soc. 112 (1990) 7984.
I. Ojima and S.Y. Lee, J. Am. Chem. Soc. 122 (2000) 2385.
I. Ojima and Z.D. Zhang, J. Organomet. Chem. 417 (1991) 253.
M. Eguchi, Q.P. Zeng, A. Korda and I. Ojima, Tetrahedron Lett. 34 (1993) 915.
I. Ojima, M. Tzamarioudaki and M. Eguchi, J. Org. Chem. 60 (1995) 7078.
I. Ojima and E.S. Vidal, J. Org. Chem. 63 (1998) 7999.
I. Ojima, D.M. Iula and M. Tzamarioudaki, Tetrahedron Lett. 39 (1998) 4599.
I. Ojima and D.M. Iula, in: The Alkaloids, Vol. 13, ed. S.W. Pelletier (Pergamon, London, 1998) p. 371.
K. Nozaki, N. Sakai, T. Nanno, T. Higashijima, S. Mano, T. Horiuchi and H. Takaya, J. Am. Chem. Soc. 119 (1997) 4413.
N. Sakai, S. Mano, K. Nozaki and H. Takaya, J. Am. Chem. Soc. 115 (1993) 7033.
Z. Hua, N. Mizutani, P.Y. Zhang and I. Ojima, in: 21st Am. Chem. Soc. National Meeting, Abstracts (2001) ORGN394.
P.Y. Zhang, S.Y. Lee and I. Ojima, in: 220th Am. Chem. Soc. National Meeting, Abstracts (2000) ORGN107.
N. Mizutani and I. Ojima, in: 221st Am. Chem. Soc. National Meeting, Abstracts (2001) ORGN395.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Ojima, I., Moralee, A.C. & Vassar, V.C. Recent Advances in Rhodium-Catalyzed Cyclization Reactions. Topics in Catalysis 19, 89–99 (2002). https://doi.org/10.1023/A:1013837417361
Issue Date:
DOI: https://doi.org/10.1023/A:1013837417361
- rhodium catalyst
- cyclization reactions
- silylformylation
- carbocyclization
- hydroformylation
- cyclohydrocarbonylation
- desymmetrization
- izidine alkaloid
- indolizidine
- silylcyclocarbonylation (SiCCa)
- silylcarbocyclization (SiCaC)
- silylcarbobicyclization (SiCaB)
- silylcarbotricyclization (SiCaT)
- cascade reaction
- Rh(acac)(CO)2
- Rh4(CO)12
- Rh2Co2(CO)12
- carbonylative carbotricyclization
- (±)-trachelanthamidine
- (±)-isoretroneconol
- (+)-prosopinine
- (−)-deoxoprosophylline
- quinolizidine
- azabicyclo[X.Y.0]alkane amino acid
- BIPHEPHOS
- BINAPHOS