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

Authors

Yuzhi Ma, Marquette University
Young K. Yun, Marquette UniversityFollow
Julie L. Wondergem, Marquette University
Anobick Sar, Marquette University
Jayapal Reddy Gone, Marquette University
Sergey V. Lindeman, Marquette UniversityFollow
William Donaldson, Marquette UniversityFollow

Document Type

Article

Language

eng

Publication Date

7-2017

Publisher

Elsevier

Source Publication

Tetrahedron

Source ISSN

0040-4020

Abstract

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 C9C16 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.

Comments

Accepted version. Tetrahedron, Vol. 73, No. 30 (July 27, 2017): 4493-4500. DOI. © 2017 Elsevier B.V. Used with permission.

Recommended Citation

Ma, Yuzhi; Yun, Young K.; Wondergem, Julie L.; Sar, Anobick; Gone, Jayapal Reddy; Lindeman, Sergey V.; and Donaldson, William, "Reactivity of (1-methoxycarbonylpentadienyl)iron(1+) cations with hydride, methyl, and nitrogen nucleophiles" (2017). Chemistry Faculty Research and Publications. 804.
https://epublications.marquette.edu/chem_fac/804