Proline-Catalyzed Sequential syn-Mannich and [4 + 1]-Annulation Cascade Reactions To Form Densely Functionalized Pyrrolidines

Proline-Catalyzed Sequential syn-Mannich and [4 + 1]-Annulation Cascade Reactions To Form Densely Functionalized Pyrrolidines

A highly efficient one-pot [4 + 1]-annulation process for the asymmetric synthesis of densely functionalized pyrrolidine derivatives is described. The in situ generated syn-Mannich adduct obtained via proline catalysis acts as a four-atom component, and Corey’s sulfur ylide or ethyl bromoacetate act...

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Veröffentlicht in:Journal of organic chemistry 2015-02, Vol.80 (3), p.2024-2031
Hauptverfasser: Aher, Ravindra D, Kumar, B. Senthil, Sudalai, Arumugam
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Catalysis
Molecular Structure
Proline - chemistry
Pyrrolidines - chemistry
Stereoisomerism
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Zusammenfassung:A highly efficient one-pot [4 + 1]-annulation process for the asymmetric synthesis of densely functionalized pyrrolidine derivatives is described. The in situ generated syn-Mannich adduct obtained via proline catalysis acts as a four-atom component, and Corey’s sulfur ylide or ethyl bromoacetate acts as a one-atom carbon source to construct pyrrolidine units in a highly enantio- and diastereoselective manner.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5028886