Literature DB >> 15373468

Asymmetric allylic alkylation, an enabling methodology.

Barry M Trost1.   

Abstract

The diversity of mechanisms for enantiodiscrimination and of bond types that can be formed make Pd-catalyzed asymmetric allylic alkylation a powerful key step for simplification of synthetic strategy to complex molecular targets. Using a wide range of different classes of compounds including alkaloids, polyhydrofurans, nucleosides and carbanucleosides, cyclohexitols and cyclopentitols, chromanes, cyclopentanoids, amino acids, barbiturates, etc., novel synthetic strategies emerge that provide short efficient asymmetric syntheses.

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Year:  2004        PMID: 15373468     DOI: 10.1021/jo0491004

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  60 in total

1.  Palladium-catalyzed allylic substitution with (η6-arene-CH2Z)Cr(CO)(3)-based nucleophiles.

Authors:  Jiadi Zhang; Corneliu Stanciu; Beibei Wang; Mahmud M Hussain; Chao-Shan Da; Patrick J Carroll; Spencer D Dreher; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2011-11-29       Impact factor: 15.419

2.  Palladium-catalyzed asymmetric allylic alkylation of electron-deficient pyrroles with meso electrophiles.

Authors:  Barry M Trost; Maksim Osipov; Guangbin Dong
Journal:  Org Lett       Date:  2012-04-16       Impact factor: 6.005

3.  Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

Authors:  Ryan L Patman; John F Bower; In Su Kim; Michael J Krische
Journal:  Aldrichimica Acta       Date:  2008       Impact factor: 3.667

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

Authors:  Sheng-Chun Sha; Hui Jiang; Jianyou Mao; Ana Bellomo; Soo A Jeong; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

5.  Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

Authors:  Seung Wook Kim; Tabitha T Schempp; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-06       Impact factor: 15.336

6.  Template-constrained macrocyclic peptides prepared from native, unprotected precursors.

Authors:  Kenneth V Lawson; Tristan E Rose; Patrick G Harran
Journal:  Proc Natl Acad Sci U S A       Date:  2013-09-16       Impact factor: 11.205

7.  Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles.

Authors:  Barry M Trost; Yong Zhang
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

8.  Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles.

Authors:  Barry M Trost; Yong Zhang
Journal:  Chemistry       Date:  2010-01-04       Impact factor: 5.236

9.  The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: reaction development, scope, and applications.

Authors:  David C Ebner; Jeffrey T Bagdanoff; Eric M Ferreira; Ryan M McFadden; Daniel D Caspi; Raissa M Trend; Brian M Stoltz
Journal:  Chemistry       Date:  2009-12-07       Impact factor: 5.236

10.  Iridium-catalyzed, regio- and enantioselective allylic substitution with aromatic and aliphatic sulfinates.

Authors:  Mitsuhiro Ueda; John F Hartwig
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

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