Literature DB >> 17625880

Asymmetric synthesis of delta-substituted alpha,beta-unsaturated delta-lactams by ring closing metathesis of enantiomerically pure N-acryloyl-homoallylic amines.

Claudio Fiorelli1, Diego Savoia.   

Abstract

Optically pure secondary homoallylic amines, obtained by highly diastereoselective addition of allylmetal reagents to imines derived from chiral amines, were N-dealkylated, and the primary amines were converted to N-acryloyl amides. Then, ring closing metathesis gave delta-substituted delta-lactams in good overall yields.

Entities:  

Year:  2007        PMID: 17625880     DOI: 10.1021/jo0703000

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

1.  Design, synthesis, and applications of chiral N-2-phenyl-2-propyl sulfinyl imines for group-assisted purification (GAP) asymmetric synthesis.

Authors:  Suresh Pindi; Jianbin Wu; Guigen Li
Journal:  J Org Chem       Date:  2013-03-26       Impact factor: 4.354

2.  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

3.  Palladium-Catalyzed Enantioselective Relay Heck Arylation of Enelactams: Accessing α,β-Unsaturated δ-Lactams.

Authors:  Qianjia Yuan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2018-05-16       Impact factor: 15.419

4.  Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin.

Authors:  Thomas J Cogswell; Craig S Donald; Rodolfo Marquez
Journal:  Beilstein J Org Chem       Date:  2020-01-28       Impact factor: 2.883

  4 in total

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