Literature DB >> 17973488

Concise construction of novel bridged bicyclic lactams by sequenced Ugi/RCM/Heck reactions.

Timothy P Ribelin1, Andrew S Judd, Irini Akritopoulou-Zanze, Rodger F Henry, Jeffrey L Cross, David N Whittern, Stevan W Djuric.   

Abstract

Herein we report a concise protocol for the diastereoselective synthesis of novel bridged bicyclic lactams from commercially available components by the sequence of Ugi, ring-closing metathesis (RCM), and Heck reactions. X-ray diffraction studies revealed that the bicyclic products contain varying degrees of pyramidalization of the bridgehead nitrogen atom.

Entities:  

Mesh:

Substances:

Year:  2007        PMID: 17973488     DOI: 10.1021/ol7023373

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


  16 in total

Review 1.  Chemistry and biology of multicomponent reactions.

Authors:  Alexander Dömling; Wei Wang; Kan Wang
Journal:  Chem Rev       Date:  2012-03-22       Impact factor: 60.622

2.  Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/N-acyliminium ion cyclization cascade.

Authors:  Steven Gunawan; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2013-08-14       Impact factor: 2.415

Review 3.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

4.  Synthesis of Diverse Heterocyclic Scaffolds via Tandem Additions to Imine Derivatives and Ring-Forming Reactions.

Authors:  James D Sunderhaus; Chris Dockendorff; Stephen F Martin
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

Review 5.  Chemistry of bridged lactams and related heterocycles.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  Chem Rev       Date:  2013-06-17       Impact factor: 60.622

6.  Towards a facile and convenient synthesis of highly functionalized indole derivatives based on multi-component reactions.

Authors:  Constantinos G Neochoritis; Alexander Dömling
Journal:  Org Biomol Chem       Date:  2014-03-14       Impact factor: 3.876

7.  Stability of medium-bridged twisted amides in aqueous solutions.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

8.  An efficient computational model to predict protonation at the amide nitrogen and reactivity along the C-N rotational pathway.

Authors:  Roman Szostak; Jeffrey Aubé; Michal Szostak
Journal:  Chem Commun (Camb)       Date:  2015-04-14       Impact factor: 6.222

9.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

10.  Proximity effects in nucleophilic addition reactions to medium-bridged twisted lactams: remarkably stable tetrahedral intermediates.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.