Literature DB >> 21283877

Efficient palladium-catalyzed asymmetric allylic alkylation of ketones and aldehydes.

Xiaohu Zhao1, Delong Liu, Fang Xie, Yangang Liu, Wanbin Zhang.   

Abstract

Palladium-catalyzed asymmetric allylic alkylation of ketones, via enamines generated in situ as nucleophiles, were carried out smoothly with chiral metallocene-based P,N-ligands. Under the same conditions, however, reactions of aldehydes could hardly be observed. Subsequently, this obstacle was resolved by using chiral metallocene-based P,P-ligands. Both ketones and aldehydes afforded excellent enantioselectivities with up to 98% ee and 94% ee, respectively.

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Year:  2011        PMID: 21283877     DOI: 10.1039/c0ob00915f

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  6 in total

1.  Synergistic Catalysis: A Powerful Synthetic Strategy for New Reaction Development.

Authors:  Anna E Allen; David W C Macmillan
Journal:  Chem Sci       Date:  2012-01-25       Impact factor: 9.825

2.  Palladium-catalyzed, pyrrolidine-mediated arylmethylation of ketones and aldehydes with coumarinyl(methyl) acetates.

Authors:  Kalicharan Cattopadhyay; Antonio Recio; Jon A Tunge
Journal:  Org Biomol Chem       Date:  2012-07-25       Impact factor: 3.876

3.  Highly selective palladium-benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions.

Authors:  Antonio Monopoli; Pietro Cotugno; Carlo Giorgio Zambonin; Francesco Ciminale; Angelo Nacci
Journal:  Beilstein J Org Chem       Date:  2015-06-10       Impact factor: 2.883

4.  Synergistic catalysis: cis-cyclopropanation of benzoxazoles.

Authors:  Marta Meazza; Mark E Light; Andrea Mazzanti; Ramon Rios
Journal:  Chem Sci       Date:  2015-10-30       Impact factor: 9.825

5.  Pd-catalyzed asymmetric allylic substitution cascade using α-(pyridin-1-yl)-acetamides formed in situ as nucleophiles.

Authors:  Kun Yao; Qianjia Yuan; Xingxin Qu; Yangang Liu; Delong Liu; Wanbin Zhang
Journal:  Chem Sci       Date:  2018-12-04       Impact factor: 9.825

Review 6.  The Allylic Alkylation of Ketone Enolates.

Authors:  Lukas Junk; Uli Kazmaier
Journal:  ChemistryOpen       Date:  2020-09-10       Impact factor: 2.630

  6 in total

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