Literature DB >> 19722547

Origin of stereoselectivity in the imidazolidinone-catalyzed reductions of cyclic alpha,beta-unsaturated ketones.

Osvaldo Gutierrez1, Robert G Iafe, K N Houk.   

Abstract

The organocatalytic transfer hydrogenation reactions of 3-phenyl-2-cyclopentenone with imidazolidinone catalysts are evaluated using the hybrid density functional (B3LYP/6-31G(d)) theory. The origin of the preference for the (E) iminium transition state is determined, and the stereoselectivity of hydride transfer is investigated.

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Year:  2009        PMID： 19722547      PMCID： PMC2751814          DOI： 10.1021/ol901586t

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


  12 in total

1.  Metal-free, organocatalytic asymmetric transfer hydrogenation of alpha,beta-unsaturated aldehydes.

Authors:  Jung Woon Yang; Maria T Hechavarria Fonseca; Nicola Vignola; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-17       Impact factor: 15.336

Review 2.  Organocatalytic hydride transfers: a new concept in asymmetric hydrogenations.

Authors:  Hans Adolfsson
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-30       Impact factor: 15.336

3.  Recent developments in asymmetric transfer hydrogenation with Hantzsch esters: a biomimetic approach.

Authors:  Shu-Li You
Journal:  Chem Asian J       Date:  2007-07-02

4.  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

5.  Highly enantioselective transfer hydrogenation of alpha,beta-unsaturated ketones.

Authors:  Nolwenn J A Martin; Benjamin List
Journal:  J Am Chem Soc       Date:  2006-10-18       Impact factor: 15.419

6.  Organocatalytic transfer hydrogenation of cyclic enones.

Authors:  Jamison B Tuttle; Stéphane G Ouellet; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2006-10-04       Impact factor: 15.419

7.  Stereoselectivity control by torsional steering in an intramolecular Diels-Alder reaction of vinyl oxocarbenium ions.

Authors:  Robert G Iafe; K N Houk
Journal:  Org Lett       Date:  2006-08-03       Impact factor: 6.005

8.  The first general enantioselective catalytic Diels-Alder reaction with simple alpha,beta-unsaturated ketones.

Authors:  Alan B Northrup; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

9.  Origin of stereoselectivity in the reduction of a planar oxacarbenium.

Authors:  Joann M Um; K N Houk; Andrew J Phillips
Journal:  Org Lett       Date:  2008-07-23       Impact factor: 6.005

Review 10.  Enantioselective organocatalytic transfer hydrogenation reactions using Hantzsch esters.

Authors:  Stéphane G Ouellet; Abbas M Walji; David W C MacMillan
Journal:  Acc Chem Res       Date:  2007-12       Impact factor: 22.384
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  2 in total

Review 1.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

2.  Oxyanion steering and CH-π interactions as key elements in an N-heterocyclic carbene-catalyzed [4 + 2] cycloaddition.

Authors:  Scott E Allen; Jessada Mahatthananchai; Jeffrey W Bode; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2012-07-16       Impact factor: 15.419
  2 in total

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