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Pearson AJ, Ghidu VP. Iron tricarbonyl stabilized pentadienyl cation as initiator for cascade polycyclizations: a diastereoselective entry into octahydrophenanthrenes. J Org Chem. 2004;69(25):8975-8doi: 10.1021/jo048557a.
Pearson, A. J., & Ghidu, V. P. (2004). Iron tricarbonyl stabilized pentadienyl cation as initiator for cascade polycyclizations: a diastereoselective entry into octahydrophenanthrenes. The Journal of organic chemistry, 69(25), 8975-8. https://doi.org/10.1021/jo048557a
Pearson, Anthony J, and Ghidu, Victor P. "Iron tricarbonyl stabilized pentadienyl cation as initiator for cascade polycyclizations: a diastereoselective entry into octahydrophenanthrenes." The Journal of organic chemistry vol. 69,25 (2004): 8975-8. doi: https://doi.org/10.1021/jo048557a
Pearson AJ, Ghidu VP. Iron tricarbonyl stabilized pentadienyl cation as initiator for cascade polycyclizations: a diastereoselective entry into octahydrophenanthrenes. J Org Chem. 2004 Dec 10;69(25):8975-8. doi: 10.1021/jo048557a. PMID: 15575788.
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J Org Chem. 2004 Dec 10;69(25):8975-8. doi: 10.1021/jo048557a.

Iron tricarbonyl stabilized pentadienyl cation as initiator for cascade polycyclizations: a diastereoselective entry into octahydrophenanthrenes.

The Journal of organic chemistry

Anthony J Pearson, Victor P Ghidu

Affiliations

  1. Case Western Reserve University, Department of Chemistry, Cleveland, OH 44106, USA. [email protected]

PMID: 15575788 DOI: 10.1021/jo048557a

Abstract

A new example is provided of completely diastereoselective polycyclization, affording the octahydrophenanthrene framework. Generation of an iron tricarbonyl stabilized pentadienyl carbocation is the triggering event of the cascade reaction. The carbocation is generated by anchimerically assisted regiospecific protonation of a double bond adjacent to the iron tricarbonyl diene moiety. Tetrafluoroboric acid ether complex appears to be the optimum reagent, affording good yields, even under catalytic conditions.

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