Synthesis and Reactivity of (Tricarbonyl)(1-ethoxycarbonyl-2-methylpentadienyl)iron(1+) Cation

Yun, Youngjun; Bärmann, Heiko; Donaldson, William A.

doi:10.1021/om0100333

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Cited by 7 publications

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“…1). 13 In the latter case, addition is observed to proceed at the C-5 pentadienyl carbon. The difference in regioselectivity can be attributed to the steric hindrance of the C-2 methyl group in 16 which is not present in cations 7 and 8 .…”

Section: Results and Discussion8mentioning

confidence: 97%

Reactivity of (1-methoxycarbonylpentadienyl)iron(1+) cations with hydride, methyl, and nitrogen nucleophiles

Yun

Wondergem

et al. 2017

Tetrahedron

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The reaction of tricarbonyl and (dicarbonyl)triphenylphosphine (1-methoxycarbonyl-pentadientyl)iron(1+) cations 7 and 8 with methyl lithium, NaBH3CN, or potassium phthalimide affords (pentenediyl)iron complexes 9a-c and 11a-b, while reaction with dimethylcuprate, gave (E,Z-diene)iron complexes 10 and 12. Oxidatively induced-reductive elimination of 9a-c gave vinylcyclopropanecarboxylates 17a-c. The optically active vinylcyclopropane (+)-17a, prepared from (1S)-7, undergoes olefin cross-metathesis with excess (+)-18 to yield (+)-19, a C9-C16 synthon for the antifungal agent ambruticin. Alternatively reaction of 7 with methanesulfonamide or trimethylsilylazide gave (E,E-diene)iron complexes 14d and e. Huisgen [3+2] cyclization of the (azidodienyl)iron complex 14e with alkynes afforded triazoles 25a-e.

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Section: Results and Discussion8mentioning

confidence: 97%