Literature DB >> 19216521

Pd(0)/InI-mediated allylic additions to 4-acetoxy-2-azetidinone: new route to highly functionalized carbocyclic scaffolds.

Cara Cesario1, Marvin J Miller.   

Abstract

Acylnitroso-derived hetero-Diels-Alder cycloadducts are susceptible to C-O bond cleavage with Pd(0) and InI to form allylic indium(III) species. The in situ prepared allylindium compounds readily react at room temperature with Eschenmoser's salt. Allylation of 4-acetoxy-2-azetidinone provides derivatized cyclopentenes in high regio- and diastereoselectivity.

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Year:  2009        PMID： 19216521      PMCID： PMC2692034          DOI： 10.1021/ol9000685

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


  7 in total

1.  Novel 1,4-benzodiazepines from acylnitroso-derived hetero-Diels-Alder cycloadducts.

Authors:  Matthew D Surman; Mark J Mulvihill; Marvin J Miller
Journal:  Org Lett       Date:  2002-01-10       Impact factor: 6.005

2.  Highly diastereoselective indium-mediated allylation of chiral hydrazones.

Authors:  Gregory R Cook; Bikash C Maity; Robert Kargbo
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005

3.  The indium-mediated selective introduction of allenyl and propargyl groups at the C4-position of 2-azetidinones and the AuCl3-catalyzed cyclization of 4-allenyl-2-azetidinones.

Authors:  Phil Ho Lee; Heechul Kim; Kooyeon Lee; Misook Kim; Kwanghyun Noh; Hyunseok Kim; Dong Seomoon
Journal:  Angew Chem Int Ed Engl       Date:  2005-03-11       Impact factor: 15.336

4.  In vitro activity of the tribactam GV104326 against gram-positive, gram-negative, and anaerobic bacteria.

Authors:  E Di Modugno; I Erbetti; L Ferrari; G Galassi; S M Hammond; L Xerri
Journal:  Antimicrob Agents Chemother       Date:  1994-10       Impact factor: 5.191

5.  A New Preparative Method for Allylic Indium(III) Reagents by Reductive Transmetalation of pi-Allylpalladium(II) with Indium(I) Salts.

Authors: 
Journal:  Org Lett       Date:  2000-03-23       Impact factor: 6.005

6.  Regio- and stereoselective ring openings of 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene systems with copper catalyst-modified grignard reagents: application to the synthesis of an inhibitor of 5-lipoxygenase.

Authors:  Matthew D Surman; Mark J Mulvihill; Marvin J Miller
Journal:  J Org Chem       Date:  2002-06-14       Impact factor: 4.354

7.  Stereo- and regioselectivity of Pd(0)/InI-mediated allylic additions to aldehydes and ketones. In situ generation of allylindium(III) intermediates from N-acylnitroso Diels-Alder cycloadducts and 1-amino-4-acetoxycyclopentenes.

Authors:  Wenlin Lee; Kyung-Hee Kim; Matthew D Surman; Marvin J Miller
Journal:  J Org Chem       Date:  2003-01-10       Impact factor: 4.354
  7 in total
  7 in total

1.  Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser's salt: One-pot preparation of diverse carbocyclic scaffolds.

Authors:  Cara Cesario; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-06-09       Impact factor: 2.415

2.  Acetoxy Meldrum's acid: a versatile acyl anion equivalent in the Pd-catalyzed asymmetric allylic alkylation.

Authors:  Barry M Trost; Maksim Osipov; Philip S J Kaib; Mark T Sorum
Journal:  Org Lett       Date:  2011-05-26       Impact factor: 6.005

3.  Cyclopropanation of nitroso Diels-Alder cycloadducts and application to the synthesis of a 2',3'-methano carbocyclic nucleoside.

Authors:  Cheng Ji; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-07-01       Impact factor: 2.415

Review 4.  The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-21       Impact factor: 15.336

5.  Indium triflate-assisted nucleophilic aromatic substitution reactions of nitrosobezene-derived cycloadducts with alcohols.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  Org Lett       Date:  2010-01-15       Impact factor: 6.005

6.  Syntheses of carbocyclic uracil polyoxin C analogs: application of Pd(0)/InI-allylation of 4-acetoxy-2-azetidinone.

Authors:  Cara Cesario; Marvin J Miller
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

7.  Regio- and stereoselective indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354
  7 in total

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