Literature DB >> 14594291

Beta-lactams or gamma-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives.

Jonathan Clayden1, David W Watson, Madeleine Helliwell, Mark Chambers.   

Abstract

Substituted acrylamide derivatives of benzylamine are lithiated alpha to nitrogen by LDA. The benzyllithium thus formed undergoes either 5-endo-trig anionic cyclisation, formally by intramolecular conjugate addition to the acrylamide, to yield 5-membered lactams, or, if the acrylamide bears a beta-electron withdrawing group, 4-exo-trig cyclisation to a beta-lactam.

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Year:  2003        PMID： 14594291     DOI： 10.1039/b308029c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  3 in total

1.  Catalytic enantioselective synthesis of indanes by a cation-directed 5-endo-trig cyclization.

Authors:  Craig P Johnston; Abhishek Kothari; Tetiana Sergeieva; Sergiy I Okovytyy; Kelvin E Jackson; Robert S Paton; Martin D Smith
Journal:  Nat Chem       Date:  2015-01-12       Impact factor: 24.427

2.  Organocatalytic Asymmetric Synthesis of Functionalized 1,3,5-Triarylpyrrolidin-2-ones via an Aza-Michael/Aldol Domino Reaction.

Authors:  Céline Joie; Kristina Deckers; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2014-03-01       Impact factor: 3.157

3.  Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative.

Authors:  Tomoko Yajima; Eriko Yoshida; Masako Hamano
Journal:  Beilstein J Org Chem       Date:  2013-07-17       Impact factor: 2.883
  3 in total

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