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Synfacts 2010(5): 0553-0553  
DOI: 10.1055/s-0029-1219707
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Dieckmann-Type Annulation

Contributor(s): Mark Lautens, Jane Panteleev
J. D. Hargrave, J. C. Allen, G. Kociok-Köhn, G. Bish, C. G. Frost*
University of Bath and Pfizer Limited, Sandwich, UK
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Publikationsdatum:
22. April 2010 (online)

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Significance

The authors disclose a rhodium-catalyzed domino reaction involving the conjugate addition of boronic acids and trapping of the ensuing enolate by an appended ester. This asymmetric strategy advances the group’s earlier work on the racemic variant of a similar reaction (Adv. Synth. Catal. 2007, 349, 432). The chiral pyrrolidine products contain quaternary stereocenters and are obtained in moderate yields and enantioselectivities.