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News


02-05-2010
Hot Paper: Catalytic Enantioselective Dieckmann-Type Annulation: Synthesis of Pyrrolidines with Quaternary Stereogenic Centers

Jonathan D. Hargrave, Joseph C. Allen, Gabriele Kociok-Köhn, Gerwyn Bish, Christopher G. Frost*

A new trick for an old dog: A Dieckmann-type cyclization was used to synthesize the title compounds with up to 96 % ee (see scheme; Bn=benzyl). The presence of a β coordinating functionality in the substrate induces a competition between cyclization and elimination pathways that is influenced by the nature of the chiral ligand. A mechanistic rationale is proposed to account for these observations.

Online veröffentlicht, DOI: 10.1002/anie.200907067

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Gesellschaft Dt. Chemiker (GDCh)Eine Zeitschrift der

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Von Angewandten-Autoren:
D. Astruc (Hrsg): Modern Arene Chemistry



 

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