Literature DB >> 19685875

Improved dienophilicity of nitrocycloalkenes: prospects for the development of a trans-Diels-Alder paradigm.

Woo Han Kim1, Jun Hee Lee, Samuel J Danishefsky.   

Abstract

The development of an efficient and stereoselective trans-Diels-Alder paradigm is described. A central element of this transformation is the introduction of a temporary dienophilic functionality (A), which serves both to activate the substrate for Diels-Alder cycloaddtion and, through its subsequent removal, to facilitate conversion of the cis-fused cycloadducts to the trans-fused series.

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Year:  2009        PMID： 19685875      PMCID： PMC2746560          DOI： 10.1021/ja9058926

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  The Type 2 Intramolecular Diels-Alder Reaction: Synthesis and Chemistry of Bridgehead Alkenes.

Authors:  Brian R. Bear; Steven M. Sparks; Kenneth J. Shea
Journal:  Angew Chem Int Ed Engl       Date:  2001-03-02       Impact factor: 15.336

2.  Catalytic Asymmetric Hetero-Diels-Alder Reactions of Carbonyl Compounds and Imines.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-10-16       Impact factor: 15.336

Review 3.  Chemistry and biology of biosynthetic Diels-Alder reactions.

Authors:  Emily M Stocking; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-14       Impact factor: 15.336

4.  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

5.  Computer-assisted design of complex organic syntheses.

Authors:  E J Corey; W T Wipke
Journal:  Science       Date:  1969-10-10       Impact factor: 47.728

Review 6.  The Diels--Alder reaction in total synthesis.

Authors:  K C Nicolaou; Scott A Snyder; Tamsyn Montagnon; Georgios Vassilikogiannakis
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

Review 7.  Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications.

Authors:  E J Corey
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

8.  Applications of total synthesis to problems in neurodegeneration: Fascinating chemistry along the way.

Authors:  Rebecca M Wilson; Samuel J Danishefsky
Journal:  Acc Chem Res       Date:  2006-08       Impact factor: 22.384

9.  Syntheses of Isomerically Pure Reference Octalins and Hydrindanes.

Authors:  Jun Hee Lee; Woo Han Kim; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-09-30       Impact factor: 2.415

10.  Enantioselective catalysis based on cationic oxazaborolidines.

Authors:  E J Corey
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
  10 in total
  11 in total

1.  An Ionic Diels-Alder Route to cis-Fused Octalins Containing an All-Carbon Quaternary Stereocenter in an Angular Position.

Authors:  Jun Hee Lee; Woo Han Kim; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2010-03-03       Impact factor: 2.415

2.  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

3.  Synthesis of Angularly Substituted trans-Fused Decalins through a Metallacycle-Mediated Annulative Cross-Coupling Cascade.

Authors:  Haruki Mizoguchi; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

4.  Enhancing the scope of the Diels-Alder reaction through isonitrile chemistry: emergence of a new class of acyl-activated dienophiles.

Authors:  Steven D Townsend; Xiangyang Wu; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-06-18       Impact factor: 15.419

5.  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

6.  Further Expansion of the trans-Diels-Alder Paradigm: Reductive Alkylation of α-Cyanoketones.

Authors:  Feng Peng; Robin E Grote; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2011-08-03       Impact factor: 2.415

7.  Origins of stereoselectivity in the trans Diels-Alder paradigm.

Authors:  Robert S Paton; Joel L Mackey; Woo Han Kim; Jun Hee Lee; Samuel J Danishefsky; K N Houk
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

8.  A Diels-Alder Route to Angularly Functionalized Bicyclic Structures.

Authors:  Woo Han Kim; Jun Hee Lee; Baptiste Aussedat; Samuel J Danishefsky
Journal:  Tetrahedron       Date:  2010-08-01       Impact factor: 2.457

9.  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

10.  A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-γ-aminated nitroalkenes derived from L-α-amino acids.

Authors:  Vera Lúcia Patrocinio Pereira; André Luiz da Silva Moura; Daniel Pais Pires Vieira; Leandro Lara de Carvalho; Eliz Regina Bueno Torres; Jeronimo da Silva Costa
Journal:  Beilstein J Org Chem       Date:  2013-04-30       Impact factor: 2.883
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