Journal
TETRAHEDRON
Volume 67, Issue 24, Pages 4318-4326Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.03.026
Keywords
C-H amination; Rh catalysis; Allenes; Cyclocarbonylation; gamma-Lactams
Categories
Funding
- University of Wisconsin, Madison
- NSF [CHE-9974839, CHE-9304546, CHE-9208463, CHE-9629688]
- NIH [RR08389-01]
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Despite their utility as building blocks for the construction of a variety of nitrogen-containing heterocyclic scaffolds, the preparation of allenic amines 2 via the direct C-H amination of allenes of the general structure 1 has not been well-explored. In this report, we describe our preliminary studies on the factors that control the chemoselectivity of Rh-catalyzed aminations of allenes to give either bicyclic methylene aziridines or the desired allenic amines 2. Additionally, the conversion of selected allenic amines to alpha,beta-unsaturated gamma-lactam scaffolds via a facile Ru-3(CO)(12) catalyzed cyclocarbonylation is described. (C) 2011 Elsevier Ltd. All rights reserved.
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