Literature DB >> 18327339

N-Heterocyclic carbene catalysed beta-lactam synthesis.

Nicolas Duguet1, Craig D Campbell, Alexandra M Z Slawin, Andrew D Smith.   

Abstract

N-Heterocyclic carbenes promote the formal [2+2] cycloaddition of ketenes with N-tosyl imines to give the corresponding beta-lactams in good to excellent isolated yields; chiral NHCs give beta-lactams in high e.e. after crystallisation.

Entities:  

Year:  2008        PMID： 18327339     DOI： 10.1039/b800857b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  16 in total

1.  Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors:  Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

2.  Chiral N-heterocyclic carbene-catalyzed generation of ester enolate equivalents from {alpha},{beta}-unsaturated aldehydes for enantioselective Diels-Alder reactions.

Authors:  Juthanat Kaeobamrung; Marisa C Kozlowski; Jeffrey W Bode
Journal:  Proc Natl Acad Sci U S A       Date:  2010-10-25       Impact factor: 11.205

Review 3.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

4.  α,β-Unsaturated acyl azoliums from N-heterocyclic carbene catalyzed reactions: observation and mechanistic investigation.

Authors:  Jessada Mahatthananchai; Pinguan Zheng; Jeffrey W Bode
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-05       Impact factor: 15.336

5.  C-H bond functionalization via hydride transfer: formation of α-arylated piperidines and 1,2,3,4-tetrahydroisoquinolines via stereoselective intramolecular amination of benzylic C-H bonds.

Authors:  Paul A Vadola; Ignacio Carrera; Dalibor Sames
Journal:  J Org Chem       Date:  2012-06-06       Impact factor: 4.354

6.  N-heterocyclic carbene-catalyzed enantioselective Mannich reactions with alpha-aryloxyacetaldehydes.

Authors:  Yasufumi Kawanaka; Eric M Phillips; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2009-12-23       Impact factor: 15.419

7.  Advances in the chemistry of β-lactam and its medicinal applications.

Authors:  Anushree Kamath; Iwao Ojima
Journal:  Tetrahedron       Date:  2012-08-07       Impact factor: 2.457

8.  Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction.

Authors:  Qijian Ni; Xiaoxiao Song; Jiawen Xiong; Gerhard Raabe; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2015-01-25       Impact factor: 6.222

9.  NHC-Catalyzed Asymmetric Synthesis of Functionalized Succinimides from Enals and α-Ketoamides.

Authors:  Lei Wang; Qijian Ni; Marcus Blümel; Tao Shu; Gerhard Raabe; Dieter Enders
Journal:  Chemistry       Date:  2015-04-15       Impact factor: 5.236

10.  Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral.

Authors:  James J Douglas; Gwydion Churchill; Alexandra M Z Slawin; David J Fox; Andrew D Smith
Journal:  Chemistry       Date:  2015-09-25       Impact factor: 5.236
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