Download PDF
Synfacts 2008(4): 0383-0383  
DOI: 10.1055/s-2008-1042790
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Intramolecular Carbonyl-Ene Cyclization

Contributor(s): Mark Lautens, Valentina Aureggi
M. L. Grachan, M. T. Tudge, E. N. Jacobsen*
Harvard University, Cambridge, USA
Further Information

Publication History

Publication Date:
19 March 2008 (online)

    Permissions and Reprints

Significance

The development of a stereoselective intramolecular carbonyl-ene reaction of simple alkenyl aldehydes catalyzed by a chiral Schiff base-Cr(III) complex is reported. The desired functionalized heterocyclic and carbocyclic products are obtained in high yields and high enantio- and diastereoselectivities. Desymmetrization of alkenyl dialdehydes and bis(alkenyl) aldehydes is also achieved in moderate to high yields with good enantioselectivities. For the preparation of the ligand, see: R. T. Ruck, E. N. Jacobsen J. Am. Chem. Soc. 2002, 124, 2882.