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Synfacts 2014; 10(1): 0047
DOI: 10.1055/s-0033-1340450
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Ni-Catalyzed Annulation of Donor–Acceptor Oxiranes with Imines

Contributor(s):
Mark Lautens
,
Christine M. Le
Zhang J, Xiao Y, Zhang J * East China Normal University, Shanghai and Shanghai Institute of Organic Chemistry, P. R. of China
Nickel-Catalyzed Annulation of Donor–Acceptor Oxiranes with Imines: Diastereoselective Access to Highly Substituted 2,4-trans-Oxazolidines.

Adv. Synth. Catal. 2013;
355: 2793-2797
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Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

donor–acceptor oxiranes - cycloaddition - nickel - oxazolidines

Significance

The use of donor–acceptor oxiranes as 1,3-dipole equivalents in cycloaddition reactions is a useful strategy for the construction of highly substituted heterocycles in a stereoselective fashion. The authors report a diastereo­selective synthesis of 2,4-trans-oxazolidines via a nickel-catalyzed [3+2] cycloaddition of donor–acceptor oxiranes and imines.


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Comment

A previous report demonstrated that donor–acceptor aziridines and aldehydes can ­undergo a [3+2] cycloaddition using a nickel ­catalyst, which furnishes 2,5-cis-oxazolidines (A. Hennig, A. Hoffmann, H. Borcherding, T. Thiele, U. Schedler, U. Resch-Genger Chem. Commun. 2011, 47, 7842). The current report represents a complementary approach towards oxazolidine scaffolds. The authors demonstrate that two electron-withdrawing groups on the oxirane are required for reactivity, suggesting that chelation to the nickel catalyst is crucial for C–C bond cleavage.


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