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Synfacts 2009(6): 0632-0632
DOI: 10.1055/s-0029-1216713
DOI: 10.1055/s-0029-1216713
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Rhodium-Catalyzed [2+2+2] Cycloaddition of Alkynes and Alkenyl Isocyanates
R. T. Yu, E. E. Lee, G. Malik, T. Rovis*
Colorado State University, Fort Collins, USA
Further Information
Publication History
Publication Date:
25 May 2009 (online)
Significance
This report presents the rhodium-catalyzed [2+2+2] cycloaddition of alkyl alkynes and alkenyl isocyanates to generate indolizidine structures in good yields and high enantioselectivities. The choice of ligand can switch the product preference from previously reported bicyclolactams to the desired indolizidines, and it is believed to be resulting from the regioselective formation of metalacycle I over IV, and subsequent CO migrations (I to II to III).