Literature DB >> 22736934

Pd and Mo Catalyzed Asymmetric Allylic Alkylation.

Barry M Trost1.   

Abstract

The ability to control the alkylation of organin>an class="Chemical">c substrates becomes ever more powerful by using metal catalysts. Among the major benefits of metal catalysis is the possibility to perform such processes asymmetrically using only catalytic amounts of the chiral inducing agent which is a ligand to the metal of the catalyst. A unique aspect of asymmetric metal catalyzed processes is the fact that many mechanisms exist for stereoinduction. Furthermore, using the same catalyst system, many types of bonds including but not limited to C-C, C-N, C-O, C-S, C-P, and C-H can be formed asymmetrically. An overview of this process using palladium and molybdenum based metals being developed in my laboratories and how they influence strategy in synthesizing bioactive molecular targets is presented.

Entities:  

Year:  2012        PMID: 22736934      PMCID: PMC3377172          DOI: 10.1021/op200294r

Source DB:  PubMed          Journal:  Org Process Res Dev        ISSN: 1083-6160            Impact factor:   3.317


  47 in total

1.  Enantioselective synthesis of (-)-codeine and (-)-morphine.

Authors:  Barry M Trost; Weiping Tang
Journal:  J Am Chem Soc       Date:  2002-12-11       Impact factor: 15.419

2.  Readily accessible chiral diene ligands for Rh-catalyzed enantioselective conjugate additions of boronic acids.

Authors:  Barry M Trost; Aaron C Burns; Thomas Tautz
Journal:  Org Lett       Date:  2011-08-11       Impact factor: 6.005

3.  Palladium-catalyzed asymmetric allylic alkylation of alpha-aryl ketones.

Authors:  Barry M Trost; Gretchen M Schroeder; Jesper Kristensen
Journal:  Angew Chem Int Ed Engl       Date:  2002-09-16       Impact factor: 15.336

4.  Dynamic kinetic asymmetric allylic amination and acyl migration of vinyl aziridines with imido carboxylates.

Authors:  Barry M Trost; Daniel R Fandrick; Tobias Brodmann; Dylan T Stiles
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  A diosphenol-based strategy for the total synthesis of (-)-terpestacin.

Authors:  Barry M Trost; Guangbin Dong; Jennifer A Vance
Journal:  J Am Chem Soc       Date:  2007-03-08       Impact factor: 15.419

6.  Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model.

Authors:  Barry M Trost; Michelle R Machacek; Aaron Aponick
Journal:  Acc Chem Res       Date:  2006-10       Impact factor: 22.384

7.  Geminal dicarboxylates as carbonyl surrogates for asymmetric synthesis. Part II. Scope and applications.

Authors:  B M Trost; C B Lee
Journal:  J Am Chem Soc       Date:  2001-04-25       Impact factor: 15.419

8.  Asymmetric synthesis of quaternary centers. Total synthesis of (-)-malyngolide.

Authors:  B M Trost; W Tang; J L Schulte
Journal:  Org Lett       Date:  2000-12-14       Impact factor: 6.005

9.  A stereodivergent strategy to both product enantiomers from the same enantiomer of a stereoinducing catalyst: agelastatin A.

Authors:  Barry M Trost; Guangbin Dong
Journal:  Chemistry       Date:  2009-07-13       Impact factor: 5.236

10.  Searching for new reactivity (Nobel lecture).

Authors:  K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2002-06-17       Impact factor: 15.336

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  19 in total

1.  Modular Approach to Degradable Acetal Polymers Using Cascade Enyne Metathesis Polymerization.

Authors:  Liangbing Fu; Xuelin Sui; Alex E Crolais; Will R Gutekunst
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-19       Impact factor: 15.336

2.  Nickel-Catalyzed Dicarbofunctionalization of Alkenes.

Authors:  Xiaoxu Qi; Tianning Diao
Journal:  ACS Catal       Date:  2020-07-02       Impact factor: 13.084

3.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

4.  Diastereoselective formation of tetrahydrofurans via Pd-catalyzed asymmetric allylic alkylation: synthesis of the C13-C29 subunit of amphidinolide N.

Authors:  Barry M Trost; Jullien Rey
Journal:  Org Lett       Date:  2012-10-25       Impact factor: 6.005

5.  Palladium-catalyzed asymmetric allylic alkylation of 3-aryloxindoles with allylidene dipivalate: a useful enol pivalate product.

Authors:  Barry M Trost; James T Masters; Aaron C Burns
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-17       Impact factor: 15.336

6.  Metal Catalyzed Allylic Alkylation: Its Development in the Trost Laboratories.

Authors:  Barry M Trost
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

7.  The Construction of All-Carbon Quaternary Stereocenters by Use of Pd-Catalyzed Asymmetric Allylic Alkylation Reactions in Total Synthesis.

Authors:  Allen Y Hong; Brian M Stoltz
Journal:  European J Org Chem       Date:  2013-05-01

8.  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

9.  A Highly Convergent Total Synthesis of Leustroducsin B.

Authors:  Barry M Trost; Berenger Biannic; Cheyenne S Brindle; B Michael O'Keefe; Thomas J Hunter; Ming-Yu Ngai
Journal:  J Am Chem Soc       Date:  2015-09-01       Impact factor: 15.419

10.  A Catalytic Asymmetric Total Synthesis of (-)-Perophoramidine.

Authors:  B M Trost; M Osipov; S Krüger; Y Zhang
Journal:  Chem Sci       Date:  2015-01-01       Impact factor: 9.825

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