Literature DB >> 10814476

Type 2 intramolecular nitroso Diels-Alder reaction. Synthesis and structure of bridgehead oxazinolactams.

S M Sparks1, J D Vargas, K J Shea.   

Abstract

[reaction--see text] The type 2 intramolecular Diels-Alder cycloaddition utilizing N-acylnitroso dienophiles provides an efficient entry into bridged oxazinolactams. In contrast to the bimolecular counterpart, the reaction is completely regioselective. Structural characterization of the cycloadducts allows for evaluation of the olefin distortion and the degree of pyramidalization of the bridgehead oxazinolactam.

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Year:  2000        PMID: 10814476     DOI: 10.1021/ol005811m

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


  6 in total

1.  Type 2 intramolecular N-acylazo Diels-Alder reaction: regio- and stereoselective synthesis of bridgehead bicyclic 1,2-diazines.

Authors:  Claudia L Molina; Chun P Chow; Kenneth J Shea
Journal:  J Org Chem       Date:  2007-08-04       Impact factor: 4.354

2.  Synthesis and evaluation of 5-lipoxygenase translocation inhibitors from acylnitroso hetero-Diels-Alder cycloadducts.

Authors:  Joshua K Bolger; Wen Tian; William R Wolter; Wonhwa Cho; Mark A Suckow; Marvin J Miller
Journal:  Org Biomol Chem       Date:  2011-03-02       Impact factor: 3.876

Review 3.  Chemistry of bridged lactams and related heterocycles.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  Chem Rev       Date:  2013-06-17       Impact factor: 60.622

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.  Stability of medium-bridged twisted amides in aqueous solutions.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

6.  Origins of regio- and stereochemistry in type 2 intramolecular N-acylnitroso Diels-Alder reactions: a computational study of tether length and substituent effects.

Authors:  Leah Cleary; Victor W Mak; Scott D Rychnovsky; Kenneth J Shea; Nicholas Sizemore
Journal:  J Org Chem       Date:  2013-03-11       Impact factor: 4.354

  6 in total

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