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

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Bibliographic Details
Title: Proline-Catalyzed Sequential syn-Mannich and [4 + 1]-Annulation Cascade Reactions To Form Densely Functionalized Pyrrolidines.
Authors: Aher, Ravindra D.1, Kumar, B. Senthil1, Sudalai, Arumugam1 a.sudalai@ncl.res.in
Source: Journal of Organic Chemistry. 2/6/2015, Vol. 80 Issue 3, p2024-2031. 8p.
Subjects: Annulation, Pyrrolidine derivatives, Mannich reaction, Pyrrolidine synthesis, Asymmetric synthesis
Abstract: 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. [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
Description
Abstract: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. [ABSTRACT FROM AUTHOR]
ISSN:00223263
DOI:10.1021/jo5028886