Literature DB >> 16928040

Direct, palladium-catalyzed, multicomponent synthesis of beta-lactams from imines, acid chloride, and carbon monoxide.

Rajiv Dhawan1, Rania D Dghaym, Daniel J St Cyr, Bruce A Arndtsen.   

Abstract

A new palladium-catalyzed synthesis of 3-amido-substituted beta-lactams is reported. This process involves the one-pot coupling of four components, imines, carbon monoxide, and acid chloride, providing a flexible route to construct this class of heterocycle. The generation of beta-lactams with two different imines can also be accomplished, providing a method to assemble these products with independent control over five separate substituents.

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Year:  2006        PMID： 16928040     DOI： 10.1021/ol061308j

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


  9 in total

1.  Mechanism and enantioselectivity in palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones: insights from computation and experiment.

Authors:  Jeffrey C Holder; Lufeng Zou; Alexander N Marziale; Peng Liu; Yu Lan; Michele Gatti; Kotaro Kikushima; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-09-27       Impact factor: 15.419

2.  VCl3 catalyzed imine-based multicomponent reactions for the facile access of functionalized tetrahydropyridines and β-amino carbonyls.

Authors:  Suman Pal; Lokman Hakim Choudhury; Tasneem Parvin
Journal:  Mol Divers       Date:  2011-11-01       Impact factor: 2.943

3.  Preparation of (S)-tert-ButylPyOx and Palladium-catalyzed Asymmetric Conjugate Addition of Arylboronic Acids.

Authors:  Jeffrey C Holder; Samantha E Shockley; Mario P Wiesenfeldt; Hideki Shimizu; Brian M Stoltz
Journal:  Organic Synth       Date:  2016-03-04

4.  Palladium-catalyzed carbonylation reactions of aryl bromides at atmospheric pressure: a general system based on Xantphos.

Authors:  Joseph R Martinelli; Donald A Watson; Dominique M M Freckmann; Timothy E Barder; Stephen L Buchwald
Journal:  J Org Chem       Date:  2008-08-23       Impact factor: 4.354

5.  Amines as key building blocks in Pd-assisted multicomponent processes.

Authors:  Didier Bouyssi; Nuno Monteiro; Geneviève Balme
Journal:  Beilstein J Org Chem       Date:  2011-10-10       Impact factor: 2.883

Review 6.  Synthetic Approaches toward Monocyclic 3-Amino-β-lactams.

Authors:  Sari Deketelaere; Tuyen Van Nguyen; Christian V Stevens; Matthias D'hooghe
Journal:  ChemistryOpen       Date:  2017-06-05       Impact factor: 2.911

7.  A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyOx) ligand.

Authors:  Hideki Shimizu; Jeffrey C Holder; Brian M Stoltz
Journal:  Beilstein J Org Chem       Date:  2013-08-12       Impact factor: 2.883

8.  Palladium-catalyzed multicomponent synthesis of 2-imidazolines from imines and acid chlorides.

Authors:  Boran Xu; Kraig Worrall; Bruce A Arndtsen
Journal:  Molecules       Date:  2012-11-22       Impact factor: 4.411

Review 9.  Recent advances in the chemistry of imine-based multicomponent reactions (MCRs).

Authors:  Lokman H Choudhury; Tasneem Parvin
Journal:  Tetrahedron       Date:  2011-07-18       Impact factor: 2.457
  9 in total

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