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

TETRAHEDRON

卷:73

Article

Ma, Yuzhi¹  Yun, Young K.¹  Wondergem (Nee Lukesh), Julie¹  Sar, Anobick¹  Gone, Jayapal Reddy¹  Lindeman, Sergey¹  Donaldson, William A.¹ 

[1] Marquette Univ, Dept Chem, POB 1881, Milwaukee, WI 53201 USA

关键词: Dienyl-iron cations;    Nucleophilic addition;    Vinylcyclopropanes;    Click chemistry;   

DOI  :  10.1016/j.tet.2017.06.026

来源: Elsevier

【 摘 要 】

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 allcynes afforded triazoles 25a-e. (C) 2017 Elsevier Ltd. All rights reserved.

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