Literature DB >> 19678681

Catalytic enantioselective allylation of dienals through the intermediacy of unsaturated pi-allyl complexes.

Ping Zhang1, James P Morken.   

Abstract

The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester [allylB(pin)] to alpha,beta,gamma,delta-unsaturated aldehydes is described. This reaction results in a remarkable inversion of substrate olefin geometry, providing the Z,E-configured reaction product in good enantioselectivity and olefin stereoselectivity. The reaction appears to proceed by conversion of the dienal to an unsaturated pi-allyl complex followed by reductive elimination via transition state II. Enantioselectivities range from 73-94% ee for a range of delta-substituted dienals when chiral ligand L3 is employed.

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Year:  2009        PMID： 19678681      PMCID： PMC2750882          DOI： 10.1021/ja9058537

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


  13 in total

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Journal:  J Am Chem Soc       Date:  2007-02-01       Impact factor: 15.419

3.  Creation of quaternary stereocenters in carbonyl allylation reactions.

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Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Stereoselective epoxidations of acyclic allylic alcohols by transition metal--hydroperoxide reagents. Synthesis of dl-C18 Cecropia juvenile hormone from farnesol.

Authors:  S Tanaka; H Yamamoto; H Nozaki; K B Sharpless; R C Michaelson; J D Cutting
Journal:  J Am Chem Soc       Date:  1974-08-07       Impact factor: 15.419

6.  Coordination of Lewis acid to eta(2)-enonepalladium(0) leading to continuous structure variation from eta(2)-olefin type to eta(3)-allyl type.

Authors:  S Ogoshi; T Yoshida; T Nishida; M Morita; H Kurosawa
Journal:  J Am Chem Soc       Date:  2001-03-07       Impact factor: 15.419

Review 7.  Phosphoramidites: marvellous ligands in catalytic asymmetric conjugate addition.

Authors:  B L Feringa
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8.  DFT studies on the mechanism of allylative dearomatization catalyzed by palladium.

Authors:  Alireza Ariafard; Zhenyang Lin
Journal:  J Am Chem Soc       Date:  2006-10-04       Impact factor: 15.419

9.  Highly enantioselective hydrosilylation of aromatic alkenes.

Authors:  Jakob F Jensen; Bo Y Svendsen; Thomas V la Cour; Henriette L Pedersen; Mogens Johannsen
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

10.  Intramolecular coupling of allyl carboxylates with allyl stannanes and allyl silanes: a new type of reductive elimination reaction?

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Journal:  Chemistry       Date:  2002-08-16       Impact factor: 5.236
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  10 in total

1.  Nickel-Catalyzed Allylic Alkylation with Diarylmethane Pronucleophiles: Reaction Development and Mechanistic Insights.

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Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

2.  Catalytic enantioselective conjugate allylation of unsaturated methylidene ketones.

Authors:  Laura A Brozek; Joshua D Sieber; James P Morken
Journal:  Org Lett       Date:  2011-02-02       Impact factor: 6.005

3.  Nickel-catalyzed reductive conjugate addition to enones via allylnickel intermediates.

Authors:  Ruja Shrestha; Stephanie C M Dorn; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

4.  Pd-catalyzed enantioselective allyl-allyl cross-coupling.

Authors:  Ping Zhang; Laura A Brozek; James P Morken
Journal:  J Am Chem Soc       Date:  2010-08-11       Impact factor: 15.419

5.  Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.

Authors:  Robert E Kyne; Michael C Ryan; Laura T Kliman; James P Morken
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

6.  Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides.

Authors:  Laura A Brozek; Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2011-10-05       Impact factor: 15.419

7.  Catalytic enantioselective allyl-allyl cross-coupling with a borylated allylboronate.

Authors:  Hai Le; Robert E Kyne; Laura A Brozek; James P Morken
Journal:  Org Lett       Date:  2013-03-19       Impact factor: 6.005

8.  Synthesis of (E,E)-Dienones and (E,E)-Dienals via Palladium-Catalyzed γ,δ-Dehydrogenation of Enones and Enals.

Authors:  Gao-Fei Pan; Xing-Long Zhang; Xue-Qing Zhu; Rui-Li Guo; Yong-Qiang Wang
Journal:  iScience       Date:  2019-09-21

9.  Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with AllylB(pin).

Authors:  Hai Le; Amanda Batten; James P Morken
Journal:  Org Lett       Date:  2014-04-04       Impact factor: 6.005

10.  Enantioselective carbocycle formation through intramolecular Pd-catalyzed allyl-aryl cross-coupling.

Authors:  Christopher H Schuster; John R Coombs; Zachary A Kasun; James P Morken
Journal:  Org Lett       Date:  2014-08-08       Impact factor: 6.005
  10 in total

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