Coenzyme-inspired chemistry 1: the C-2 alkylation of 4,5-dihydroimidazoles

Coenzyme-inspired chemistry 1: the C-2 alkylation of 4,5-dihydroimidazoles

Alkylation of 4,5-dihydroimidazoles at C-2 is accomplished using a double umpolung of the reactivity of that position, via sulfenylation of a nucleophilic C-2 lithio-species and substitution using an alkyl nucleophile. Arylation via unexpected sulfide contraction from the arylsulfenylation products...

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Veröffentlicht in:Tetrahedron 2013-05, Vol.69 (20), p.4114-4119
Hauptverfasser: Jones, Raymond C.F., Nichols, John R.
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
C1-transfer
Cleavage
Coenzyme mimic
Dihydroimidazole
Nucleophiles
Sulfides
Tetrahedrons
Tetrahydrofolate
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Zusammenfassung:Alkylation of 4,5-dihydroimidazoles at C-2 is accomplished using a double umpolung of the reactivity of that position, via sulfenylation of a nucleophilic C-2 lithio-species and substitution using an alkyl nucleophile. Arylation via unexpected sulfide contraction from the arylsulfenylation products has also been demonstrated. Taken with dihydroimidazole cleavage protocols, this constitutes a tetrahydrofolate-inspired C1-transfer protocol. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.03.040