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 |
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| container_title | Tetrahedron |
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| creator | Jones, Raymond C.F. Nichols, John R. |
| description | 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.
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| doi_str_mv | 10.1016/j.tet.2013.03.040 |
| format | Article |
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| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2013-05, Vol.69 (20), p.4114-4119 |
| issn | 0040-4020 1464-5416 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1744704086 |
| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Alkylation C1-transfer Cleavage Coenzyme mimic Dihydroimidazole Nucleophiles Sulfides Tetrahedrons Tetrahydrofolate |
| title | Coenzyme-inspired chemistry 1: the C-2 alkylation of 4,5-dihydroimidazoles |
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