Literature DB >> 21309528

Stereospecific ring expansion of chiral vinyl aziridines.

Matthew Brichacek1, Mauricio Navarro Villalobos, Alexandra Plichta, Jon T Njardarson.   

Abstract

In this report, it is demonstrated that chiral vinyl aziridines can be stereospecifically ring expanded. This synthetic approach allows controlled access to chiral 2,5-cis- or 2,5-trans-3-pyrroline products from starting materials with the appropriate aziridine geometry. Twenty three ring expansion examples, most of which feature a stereospecific cyclization, are presented.

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Year:  2011        PMID: 21309528      PMCID: PMC3072884          DOI: 10.1021/ol200263g

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


  15 in total

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5.  Enantioselective, palladium-catalyzed alpha-arylation of N-Boc-pyrrolidine.

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6.  Asymmetric synthesis of unsaturated, fused bicyclic proline analogues through amino alkylation of cyclic bis(allylsulfoximine)titanium complexes and migratory cyclization of delta-amino alkenyl aminosulfoxonium salts.

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7.  Asymmetric synthesis of trans-2,5-disubstituted pyrrolidines from enantiopure homoallylic amines. Synthesis of pyrrolidine (-)-197B.

Authors:  Franklin A Davis; Minsoo Song; Alexander Augustine
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354

8.  Asymmetric synthesis of fused bicyclic alpha-amino acids having a hexahydro-cyclopenta[c]pyridine skeleton via intramolecular Pauson-Khand reaction of 1-sulfonimidoyl-substituted 5-azaoct-1-en-7-ynes.

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10.  Practical and highly selective sulfur ylide mediated asymmetric epoxidations and aziridinations using an inexpensive, readily available chiral sulfide. Applications to the synthesis of quinine and quinidine.

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  6 in total

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2.  Site-Selective Nitrene Transfer to Conjugated Olefins Directed by Oxazoline Peptide Ligands.

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Review 3.  Metal-mediated synthesis of pyrrolines.

Authors:  Noelia S Medran; Agustina La-Venia; Sebastian A Testero
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4.  Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines.

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5.  Ring expansion of vinylaziridines through the strain-release pericyclic reaction: recent developments and applications.

Authors:  Yu Mi Heo; Seung-Mann Paek
Journal:  Molecules       Date:  2013-08-12       Impact factor: 4.411

6.  Intermolecular [3+3] ring expansion of aziridines to dehydropiperi-dines through the intermediacy of aziridinium ylides.

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  6 in total

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