Literature DB >> 23151095

Halocycloalkenones as Diels-Alder dienophiles. Applications to generating useful structural patterns.

Audrey G Ross1, Steven D Townsend, Samuel J Danishefsky.   

Abstract

Halocycloalkenones are demonstrated to function as potent dienophiles in inter- and intramolecular Diels-Alder cycloadditions. We have found 2-brominated cycloalkenone dienophiles to be both highly endo selective and significantly more reactive than their nonhalogenated parent compounds. A method for the facile conversion of brominated cyclobutanone DA adducts to synthetically useful cyclopropyl functional handles is described.

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Year:  2012        PMID： 23151095      PMCID： PMC3543988          DOI： 10.1021/jo302230m

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


  6 in total

1.  Pattern recognition in retrosynthetic analysis: snapshots in total synthesis.

Authors:  Rebecca M Wilson; Samuel J Danishefsky
Journal:  J Org Chem       Date:  2007-06-08       Impact factor: 4.354

2.  A straightforward route to functionalized trans-Diels-Alder motifs.

Authors:  Jun Hee Lee; Yandong Zhang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

3.  Diels-Alder routes to angularly halogenated cis-fused bicyclic ketones: Readily accessible cyclynone intermediates.

Authors:  Jun Hee Lee; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2010-09-01       Impact factor: 2.415

4.  Cyclobutenone as a highly reactive dienophile: expanding upon Diels-Alder paradigms.

Authors:  Xiaohua Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

5.  Synthesis of stable derivatives of cycloprop-2-ene carboxylic acid.

Authors:  Ni Yan; Xiaozhong Liu; Mahesh K Pallerla; Joseph M Fox
Journal:  J Org Chem       Date:  2008-05-02       Impact factor: 4.354

6.  Intramolecular Diels-Alder reactions of cycloalkenones: translation of high endo selectivity to trans junctions.

Authors:  Audrey G Ross; Xiaohua Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-09-18       Impact factor: 15.419
  6 in total
  4 in total

1.  Pattern recognition analysis in complex molecule synthesis and the preparation of iso-Diels-Alder motifs.

Authors:  Feng Peng; Robin E Grote; Rebecca M Wilson; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2013-06-19       Impact factor: 11.205

2.  Stereospecific cis- and trans-ring fusions arising from common intermediates.

Authors:  Steven D Townsend; Audrey G Ross; Kai Liu; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2014-05-19       Impact factor: 11.205

3.  Intramolecular Diels-Alder reactions of cycloalkenones: stereoselectivity, Lewis acid acceleration, and halogen substituent effects.

Authors:  Hung V Pham; Robert S Paton; Audrey G Ross; Samuel J Danishefsky; K N Houk
Journal:  J Am Chem Soc       Date:  2014-02-04       Impact factor: 15.419

4.  Asymmetric Synthesis of Tertiary α -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution.

Authors:  Mei Kee Kam; Akira Sugiyama; Ryouta Kawanishi; Kazutaka Shibatomi
Journal:  Molecules       Date:  2020-08-27       Impact factor: 4.411
  4 in total

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