Functionalized 4-Carboxy- and 4-Keto-2,3-dihydropyrroles via Ni(II)-Catalyzed Nucleophilic Amine Ring-Opening Cyclizations of Cyclopropanes
M. Cynthia Martin, Dadasaheb V. Patil and Stefan France*
*School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States, Email: stefan.francechemistry.gatech.edu
M. C. Martin. D. V. Patil, S. France, J. Org. Chem., 2014, 79, 3030-3039.
DOI: 10.1021/jo5001059 (free Supporting Information)
see article for more reactions
Ni(ClO4)2·6H2O can be used as a Lewis acid catalyst for nucleophilic amine ring-opening cyclizations of donor-acceptor (D-A) cyclopropanes to yield vinylogous 4-carboxy- and 4-keto-2,3-dihydropyrroles in good yields under milder reaction conditions than previously reported. The reaction is amenable to a variety of D-A cyclopropanes and primary amines.
see article for more examples