Literature DB >> 22630569

Why a proximity-induced Diels-Alder reaction is so fast.

Elizabeth H Krenske1, Emma W Perry, Steven V Jerome, Thomas J Maimone, Phil S Baran, K N Houk.   

Abstract

Unlike normal Diels-Alder reactions of acyclic alkadienes with alkenes, the vinylbicyclo[2.2.2]octene employed in the Baran total synthesis of vinigrol undergoes a quantitative Diels-Alder reaction with a tethered alkene at room temperature. Density functional theory calculations reveal that this unprecedented reactivity originates from a combination of preorganization, diene strain, and tether stabilization.

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Year:  2012        PMID： 22630569      PMCID： PMC3426630          DOI： 10.1021/ol301083q

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


  11 in total

1.  Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model.

Authors:  Maurizio Cossi; Nadia Rega; Giovanni Scalmani; Vincenzo Barone
Journal:  J Comput Chem       Date:  2003-04-30       Impact factor: 3.376

2.  Reverse cope elimination of hydroxylamines and alkenes or alkynes: theoretical investigation of tether length and substituent effects.

Authors:  Elizabeth H Krenske; Edwin C Davison; Ian T Forbes; Jacqueline A Warner; Adrian L Smith; Andrew B Holmes; K N Houk
Journal:  J Am Chem Soc       Date:  2012-01-17       Impact factor: 15.419

3.  Synthesis of the tricyclic core of vinigrol via an intramolecular Diels-Alder reaction.

Authors:  Christiane M Grisé; Guillaume Tessier; Louis Barriault
Journal:  Org Lett       Date:  2007-03-16       Impact factor: 6.005

4.  A concise approach to vinigrol.

Authors:  Thomas J Maimone; Ana-Florina Voica; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Distortion/interaction energy control of 1,3-dipolar cycloaddition reactivity.

Authors:  Daniel H Ess; K N Houk
Journal:  J Am Chem Soc       Date:  2007-08-09       Impact factor: 15.419

6.  Density functionals with broad applicability in chemistry.

Authors:  Yan Zhao; Donald G Truhlar
Journal:  Acc Chem Res       Date:  2008-01-11       Impact factor: 22.384

7.  Transition state distortion energies correlate with activation energies of 1,4-dihydrogenations and Diels-Alder cycloadditions of aromatic molecules.

Authors:  Amy E Hayden; K N Houk
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419

8.  Total synthesis of vinigrol.

Authors:  Thomas J Maimone; Jun Shi; Shinji Ashida; Phil S Baran
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

9.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

Authors: 
Journal:  Phys Rev B Condens Matter       Date:  1988-01-15

10.  Experimental Diels-Alder reactivities of cycloalkenones and cyclic dienes explained through transition-state distortion energies.

Authors:  Robert S Paton; Seonah Kim; Audrey G Ross; Samuel J Danishefsky; K N Houk
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-09       Impact factor: 15.336
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  6 in total

1.  Synthetic Approaches and Total Syntheses of Vinigrol, a Unique Diterpenoid.

Authors:  Cristian Draghici; Jon T Njardarson
Journal:  Tetrahedron       Date:  2015-06-10       Impact factor: 2.457

2.  Total synthesis of taxane terpenes: cyclase phase.

Authors:  Yoshihiro Ishihara; Abraham Mendoza; Phil S Baran
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

3.  Enantioselective total synthesis of the reported structures of (-)-9-epi-presilphiperfolan-1-ol and (-)-presilphiperfolan-1-ol: structural confirmation and reassignment and biosynthetic insights.

Authors:  Allen Y Hong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-22       Impact factor: 15.336

Review 4.  Syntheses of Complex Terpenes from Simple Polyprenyl Precursors.

Authors:  Claire S Harmange Magnani; Danny Q Thach; Karl T Haelsig; Thomas J Maimone
Journal:  Acc Chem Res       Date:  2020-03-23       Impact factor: 22.384

5.  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

6.  On the catalytic effect of water in the intramolecular Diels–Alder reaction of quinone systems: a theoretical study.

Authors:  Jorge Soto-Delgado; Arie Aizman; Renato Contreras; Luis R Domingo
Journal:  Molecules       Date:  2012-11-20       Impact factor: 4.411
  6 in total

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