Synthesis of substituted 2-aminoimidazoles via Pd-catalyzed alkyne carboamination reactions. Application to the synthesis of preclathridine natural products.

Autor: Zavesky BP; Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109-1005, United States., Babij NR, Wolfe JP
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2014 Sep 19; Vol. 16 (18), pp. 4952-5. Date of Electronic Publication: 2014 Sep 08.
DOI: 10.1021/ol502471x
Abstrakt: A new method for the synthesis of 2-aminoimidazole products is described. The heterocyclic products are generated in good yields via Pd-catalyzed carboamination reactions of N-propargyl guanidines and aryl triflates. This methodology generates both a C-N and C-C bond during the annulation step and facilitates the rapid construction of 2-aminoimidazole products with different aryl groups. The utility of this methodology was demonstrated in the total synthesis of preclathridine A, preclathridine B, and dorimidazole B from a single intermediate.
Databáze: MEDLINE