Samarium diiodide-promoted intramolecular radical cyclization of (η4-diene)Fe(CO)3 complexes bearing keto side chains

Ming-Chang P. Yeh, Fu Chun Wang, Jin Juean Tu, Sun Chi Chang, Cheng Chiang Chou, Jin Wei Liao

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Abstract

Reaction of samarium diiodide with (η4-cyclohexadiene)Fe(CO)3 complexes bearing keto side chains in THF/HMPA/t-BuOH gives fused bicyclo[4.3.0]nonenol derivatives, whereas (η4-cycloheptadiene)Fe(CO)3 analogues produce a bicyclo[5.3.0]decenol ring skeleton. The iron-mediated intramolecular radical addition allows for the direct stereocontrol of three contiguous stereogenic centers of these fused bicyclic skeletons. Under the same reaction conditions, intramolecular ketyl radical cyclization of acyclic (η4-1,3-butadiene)Fe(CO)3 complexes with keto side chains at the terminal position of the diene ligands furnishes disubstituted cyclopentanol and cyclohexanol derivatives with excellent diastereoselectivity.

Original languageEnglish
Pages (from-to)5656-5662
Number of pages7
JournalOrganometallics
Volume17
Issue number26
Publication statusPublished - 1998 Dec 1

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Yeh, M-C. P., Wang, F. C., Tu, J. J., Chang, S. C., Chou, C. C., & Liao, J. W. (1998). Samarium diiodide-promoted intramolecular radical cyclization of (η4-diene)Fe(CO)3 complexes bearing keto side chains. Organometallics, 17(26), 5656-5662.