Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

Huang, Zhiyuan; Phelan, Zaki K.; Tritt, Rachel L.; Valent, Shelby D.; Guan, Ziyang; He, Yiqun; Weiss, Philip; Griffith, Daniel R.

doi:10.3791/60050-v

Cited by 2 publications

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“…As shown in Scheme 2a , the synthesis of the requisite Heck reaction precursor began with the addition of the known allylic amine 5 to tricarbonyl(tropone)iron, immediately followed by Boc-protection of the crude secondary amine according to our previously described, solvent-free protocol [ 12 – 13 ]. The resulting iron complex 6 was demetallated upon irradiation with UV light [ 14 ] to give the deconjugated olefin 7 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

Shoemaker,

Foker,

Uttaro

et al. 2023

Beilstein J. Org. Chem.

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The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η4-diene complex with Fe(CO)3) in a short sequence of steps: 1) nucleophilic amine addition and subsequent Boc-protection, 2) photochemical demetallation of the iron complex, and 3) an intramolecular Heck reaction. Minor modifications to the protocol enabled access to the related 2-azabicyclo[4.4.1]undecane system, albeit in lower yield.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

Shoemaker,

Foker,

Uttaro

et al. 2023

Beilstein J. Org. Chem.

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show abstract

“…As shown in Scheme 2a, the synthesis of the requisite Heck reaction precursor began the addition of the known allylic amine 5 to tricarbonyl(tropone)iron, immediately followed by Boc-protection of the crude secondary amine according to our previously described, solvent-free protocol [12,13]. The resulting iron complex 6 was demetallated upon irradiation with UV light [14] to give the deconjugated olefin 7.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 7-azabicyclo[4.3.1]decane ring system from tricarbonyl(tropone)iron via intramolecular Heck reactions

Shoemaker,

Foker,

Uttaro

et al. 2023

Preprint

View full text Add to dashboard Cite

The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η4-diene complex with Fe(CO)3) in a short sequence of steps: 1) nucleophilic amine addition and subsequent Boc-protection; 2) photochemical demetallation of the iron complex; 3) intramolecular Heck reaction. Minor modifications to the protocol enabled access to the related 2-azabicyclo[4.4.1]undecane and 8-azabicyclo[5.3.0]decane ring systems, albeit in lower yield.

show abstract

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

Cited by 2 publications

References 0 publications

Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

Synthesis of 7-azabicyclo[4.3.1]decane ring system from tricarbonyl(tropone)iron via intramolecular Heck reactions

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