Ni-Catalyzed Annulation of Donor–Acceptor Oxiranes with Imines

Mark Lautens; Christine M. Le

doi:10.1055/s-0033-1340450

Synfacts, Table of Contents

Synfacts 2014; 10(1): 0047
DOI: 10.1055/s-0033-1340450

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Ni-Catalyzed Annulation of Donor–Acceptor Oxiranes with Imines

Contributor(s):

Mark Lautens

,

Christine M. Le

Abstract

Full Text

PDF Download

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

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.

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.

Figures