Synfacts 2006(3): 0256-0256  
DOI: 10.1055/s-2006-932023
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Catalytic Enantioselective Conia-Ene Reaction

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
B. K. Corkey, F. D. Toste*
University of California, Berkeley, USA
Further Information

Publication History

Publication Date:
21 February 2006 (online)

Significance

The authors describe the first asymmetric intramolecular Conia-ene reaction of β-dicarbonyl compounds and alkynes. The use of palladium on the bidentate phosphine gave the best yields and selectivities when combined with ytterbium triflate and AcOH. Only compounds with R1 = Ar gave good enantioselectivities (>70%) whereas compounds with alkoxy substituents in R2 position gave products with higher selectivity compared to those with R2 = Alk.