Synfacts 2008(2): 0171-0171  
DOI: 10.1055/s-2007-992447
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Novel Reagent for Palladium-Catalyzed Cycloaddition with Nitrones

Contributor(s): Hisashi Yamamoto, Marina Naodovic
R. Shintani, M. Murakami, T. Hayashi*
Kyoto University, Japan
Further Information

Publication History

Publication Date:
23 January 2008 (online)


Hayashi’s group introduced a novel coupling partner for the asymmetric Pd-catalyzed [4+3] cycloaddition. In the presence of chiral phosphoramidite ligand 1, γ-methylidene-δ-valerolactone undergoes cycloaddition with nitrones to furnish adducts in high yields and excellent selectivity. Furthermore, it was shown that reagent 2 exhibits comparably good reactivity towards azamethine imines as well. A significant feature of this protocol is the installment of two contiguous tertiary and quaternary stereocenters.