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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)



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Abstract

Ni(ClO4)26H2O 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.

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Key Words

2-Pyrrolines


ID: J42-Y2014