Literature DB >> 16898782

Asymmetric multicomponent [C+NC+CC] synthesis of highly functionalized pyrrolidines catalyzed by silver(I).

Philip Garner1, H Umit Kaniskan, Jieyu Hu, Wiley J Youngs, Matthew Panzner.   

Abstract

[reaction: see text] Highly functionalized pyrrolidines are obtained in a single chemical step via a mild, efficient, and selective Ag(I)-catalyzed asymmetric [C+NC+CC] coupling process. Oppolzer's camphorsultam enables the desired reaction cascade and provides a reliable means to control the developing stereochemistry and purify the products. This three-component reaction provides unprecedented access to structurally diverse pyrrolidines for both target- and diversity-oriented syntheses.

Entities:  

Year:  2006        PMID: 16898782     DOI: 10.1021/ol061113b

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid.

Authors:  Erik C Carlson; Lauren K Rathbone; Hua Yang; Nathan D Collett; Rich G Carter
Journal:  J Org Chem       Date:  2008-06-05       Impact factor: 4.354

2.  Design and Synthesis of Pyrrolidine-based Fragments That Sample Three-dimensional Molecular Space.

Authors:  Philip Garner; Philip B Cox; Upendra Rathnayake; Nicholas Holloran; Paul Erdman
Journal:  ACS Med Chem Lett       Date:  2019-04-12       Impact factor: 4.345

Review 3.  Silver and gold-catalyzed multicomponent reactions.

Authors:  Giorgio Abbiati; Elisabetta Rossi
Journal:  Beilstein J Org Chem       Date:  2014-02-26       Impact factor: 2.883

  3 in total

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