Literature DB >> 17637953

Synthesis of alpha,beta-unsaturated gamma-lactams via asymmetric iridium-catalysed allylic substitution.

Stephanie Spiess1, Carola Berthold, Robert Weihofen, Günter Helmchen.   

Abstract

Syntheses of alpha,beta-unsaturated gamma-lactams are described that are based on ring-closing metathesis in combination with enantioselective Ir-catalysed allylic amination using N-Boc-N-(but-2-enoyl)-amine as a pronucleophile. As an example application, the synthesis of a Baclofen analogue is presented.

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Year:  2007        PMID： 17637953     DOI： 10.1039/b708571k

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


  6 in total

1.  Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

Authors:  Seung Wook Kim; Tabitha T Schempp; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-06       Impact factor: 15.336

2.  Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines.

Authors:  Seung Wook Kim; Leyah A Schwartz; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

3.  Amphiphilic π-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups.

Authors:  Arismel Tena Meza; Thomas Wurm; Lewis Smith; Seung Wook Kim; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-01-19       Impact factor: 15.419

4.  Chiral oxazolidinones as electrophiles: Intramolecular cyclization reactions with carbanions and preparation of functionalized lactams.

Authors:  Sarah Gibson; Hollie K Jacobs; Aravamudan S Gopalan
Journal:  Tetrahedron Lett       Date:  2011-02-23       Impact factor: 2.415

5.  A mild and efficient approach to enantioenriched α-hydroxyethyl α,β-unsaturated δ-lactams.

Authors:  Seo-Jung Han; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2016-05-25       Impact factor: 2.415

6.  Regio- and enantioselective N-allylations of imidazole, benzimidazole, and purine heterocycles catalyzed by single-component metallacyclic iridium complexes.

Authors:  Levi M Stanley; John F Hartwig
Journal:  J Am Chem Soc       Date:  2009-07-01       Impact factor: 15.419
  6 in total

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