Literature DB >> 20160837

Brønsted acid-mediated opening of nitroso cycloadducts under anhydrous conditions.

Brian S Bodnar1, Marvin J Miller.   

Abstract

An unusual bicyclic hydroxamate resulted from C-O bond cleavage of acylnitroso hetero-Diels-Alder cycloadducts when treated with catalytic Brønsted acids under anhydrous conditions. Similarly, the formation of a nitrone was observed using one equivalent of triflic acid.

Entities:  

Year:  2009        PMID： 20160837      PMCID： PMC2613285          DOI： 10.1016/j.tetlet.2008.11.120

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  8 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.  The Hetero Diels-Alder Reactions between D-Mannose-Derived Halonitroso Compounds and Cyclopentadiene: Scope and Limitations.

Authors:  Deyi Zhang; Carsten Süling; Marvin J. Miller
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

3.  Stereoselective total synthesis of (+)-streptazolin by using a temporary silicon-tethered RCM strategy.

Authors:  Fangzheng Li; Marvin J Miller
Journal:  J Org Chem       Date:  2006-07-07       Impact factor: 4.354

4.  Regio- and stereochemically controlled formation of hydroxamic acid containing anti- or syn-1,4-cycloalkenols from acylnitroso-derived Diels-Alder adducts.

Authors:  M D Surman; M J Miller
Journal:  J Org Chem       Date:  2001-04-06       Impact factor: 4.354

5.  Synthetic application of acylnitroso Diels-Alder derived aminocyclopentenols: total synthesis of (+)-streptazolin.

Authors:  Fangzheng Li; Namal C Warshakoon; Marvin J Miller
Journal:  J Org Chem       Date:  2004-12-10       Impact factor: 4.354

6.  Chemoenzymatic synthesis and synthetic application of enantiopure aminocyclopentenols: total synthesis of carbocyclic (+)-uracil polyoxin C and its alpha-epimer.

Authors:  Fangzheng Li; John B Brogan; Jennifer L Gage; Deyi Zhang; Marvin J Miller
Journal:  J Org Chem       Date:  2004-06-25       Impact factor: 4.354

7.  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

8.  Reactions of nitroso hetero-Diels-Alder cycloadducts with azides: stereoselective formation of triazolines and aziridines.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  J Org Chem       Date:  2007-04-13       Impact factor: 4.354
  8 in total
  4 in total

1.  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 2.  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

3.  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

4.  Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents.

Authors:  Hisato Shimizu; Akira Yoshimura; Keiichi Noguchi; Victor N Nemykin; Viktor V Zhdankin; Akio Saito
Journal:  Beilstein J Org Chem       Date:  2018-02-28       Impact factor: 2.883
  4 in total

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