Synfacts 2010(6): 0665-0665  
DOI: 10.1055/s-0029-1219857
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Azomethine Ylide Cycloadditions with ThioClickFerrophos Ligands

Contributor(s): Mark Lautens, Stephen G. Newman
I. Oura, K. Shimizu, K. Ogata, S.-i. Fukuzawa*
Chuo University, Tokyo, Japan
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Publikationsverlauf

Publikationsdatum:
20. Mai 2010 (online)

Significance

Chiral pyrrolidines play an important role as synthetic intermediates and organocatalysts. These heterocycles can be accessed rapidly by a 1,3-dipolar cycloaddition between azomethine ylides and electron-deficient alkenes, such as unsaturated esters, vinyl sulfones, and ­nitroalkenes. In addition to enantioselectivity, the control of endo versus exo selectivity is crucial. Utilizing their previously prepared ThioClickFerrophos ligands (M. Kato et al. Eur. J. Org. Chem. 2009, 5232), the authors have developed the first endo-selective dipolar cycloaddition between acyclic α,β-unsaturated ketones and azomethine ylides.