Synfacts 2009(11): 1244-1244  
DOI: 10.1055/s-0029-1218127
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Syntheses of Enantiopure Bicyclic Oxazolidines Using Pd(II) Catalysts

Contributor(s): Mark Lautens, Chit Tsui
J. Alladoum, E. Vrancken, P. Mangeney, S. Roland*, C. Kadouri-Puchot*
Université Pierre et Marie Curie - Paris 6, France
Further Information

Publication History

Publication Date:
22 October 2009 (online)

Significance

Bicyclic oxazolidines are important intermediates in synthetic chemistry serving, for example, as valuable building blocks for nitrogen-containing heterocycles that belong to a class of biologically active compounds. Building on previous studies of the diastereoselective synthesis of various β-amino alcohols, the authors report herein a new palladium(II)-catalyzed cyclization of chiral unsaturated β-amino alcohols to afford enantiopure bicyclic oxazolidines with total regio- and stereocontrol.