Literature DB >> 27960315

Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer.

Eiji Yamamoto1, Margaret J Hilton1, Manuel Orlandi1, Vaneet Saini1, F Dean Toste2, Matthew S Sigman1.   

Abstract

Enantioselective 1,1-diarylation of terminal alkenes enabled by the combination of Pd catalysis with a chiral anion phase transfer (CAPT) strategy is reported herein. The reaction of substituted benzyl acrylates with aryldiazonium salts and arylboronic acids gave the corresponding 3,3-diarylpropanoates in moderate to good yields with high enantioselectivies (up to 98:2 er). Substituents on the benzyl acrylate and CAPT catalyst significantly affect the enantioselectivity, and multidimensional parametrization identified correlations suggesting structural origins for the high stereocontrol.

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Year:  2016        PMID： 27960315      PMCID： PMC5217716          DOI： 10.1021/jacs.6b11367

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


  34 in total

1.  Facile domino access to chiral bicyclo[3.2.1]octanes and discovery of a new catalytic activation mode.

Authors:  Bin Tan; Yunpeng Lu; Xiaofei Zeng; Pei Juan Chua; Guofu Zhong
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

2.  Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts.

Authors:  Albrecht Berkessel; Felix Cleemann; Santanu Mukherjee; Thomas N Müller; Johann Lex
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-21       Impact factor: 15.336

3.  Chemoenzymatic synthesis and application of bicyclo[2.2.2]octadiene ligands: increased efficiency in rhodium-catalyzed asymmetric conjugate additions by electronic tuning.

Authors:  Yunfei Luo; Andrew J Carnell
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-01       Impact factor: 15.336

4.  Aromatic interactions as control elements in stereoselective organic reactions.

Authors:  Elizabeth H Krenske; K N Houk
Journal:  Acc Chem Res       Date:  2012-07-24       Impact factor: 22.384

5.  A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

Authors:  Longyan Liao; Ranjan Jana; Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

6.  Catalytic asymmetric synthesis with rh-diene complexes: 1,4-addition of arylboronic acids to unsaturated esters.

Authors:  Jean-François Paquin; Corey R J Stephenson; Christian Defieber; Erick M Carreira
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

7.  Catalytic Asymmetric Arylation of α-Aryl-α-diazoacetates with Aniline Derivatives.

Authors:  Bin Xu; Mao-Lin Li; Xiao-Dong Zuo; Shou-Fei Zhu; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2015-07-06       Impact factor: 15.419

8.  Neurochemical profile of Lu 19-005, a potent inhibitor of uptake of dopamine, noradrenaline, and serotonin.

Authors:  J Hyttel; J J Larsen
Journal:  J Neurochem       Date:  1985-05       Impact factor: 5.372

9.  Enantio- and diastereoselective Michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea.

Authors:  Tomotaka Okino; Yasutaka Hoashi; Tomihiro Furukawa; Xuenong Xu; Yoshiji Takemoto
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

10.  Development of a screen to identify selective small molecules active against patient-derived metastatic and chemoresistant breast cancer cells.

Authors:  Keith M Gligorich; Rachel M Vaden; Dawne N Shelton; Guoying Wang; Cindy B Matsen; Ryan E Looper; Matthew S Sigman; Bryan E Welm
Journal:  Breast Cancer Res       Date:  2013       Impact factor: 6.466
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  24 in total

1.  Harnessing Noncovalent Interactions in Dual-Catalytic Enantioselective Heck-Matsuda Arylation.

Authors:  Yernaidu Reddi; Cheng-Che Tsai; Carolina M Avila; F Dean Toste; Raghavan B Sunoj
Journal:  J Am Chem Soc       Date:  2018-12-28       Impact factor: 15.419

2.  Mechanistic Investigations of the Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Benzyl Acrylates.

Authors:  Manuel Orlandi; Margaret J Hilton; Eiji Yamamoto; F Dean Toste; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2017-08-30       Impact factor: 15.419

3.  Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis.

Authors:  Souvagya Biswas; Koji Kubota; Manuel Orlandi; Mathias Turberg; Dillon H Miles; Matthew S Sigman; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-12       Impact factor: 15.336

4.  Interrogation of 2,2'-Bipyrimidines as Low-Potential Two-Electron Electrolytes.

Authors:  Jeremy D Griffin; Adam R Pancoast; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2021-01-07       Impact factor: 15.419

5.  Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis.

Authors:  F Dean Toste; Matthew S Sigman; Scott J Miller
Journal:  Acc Chem Res       Date:  2017-03-21       Impact factor: 22.384

6.  Parametrization of Non-covalent Interactions for Transition State Interrogation Applied to Asymmetric Catalysis.

Authors:  Manuel Orlandi; Jaime A S Coelho; Margaret J Hilton; F Dean Toste; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2017-05-11       Impact factor: 15.419

7.  Multidimensional Correlations in Asymmetric Catalysis through Parameterization of Uncatalyzed Transition States.

Authors:  Manuel Orlandi; F Dean Toste; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-04       Impact factor: 15.336

8.  Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis.

Authors:  Banruo Huang; Ying He; Mark D Levin; Jaime A S Coelho; Robert G Bergman; F Dean Toste
Journal:  Adv Synth Catal       Date:  2019-09-06       Impact factor: 5.837

9.  Quantitative Modeling of Bis(pyridine)silver(I) Permanganate Oxidation of Hydantoin Derivatives: Guidelines for Predicting the Site of Oxidation in Complex Substrates.

Authors:  Amanda J Bischoff; Brandon M Nelson; Zachary L Niemeyer; Matthew S Sigman; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2017-10-18       Impact factor: 15.419

Review 10.  Quantitative Structure-Selectivity Relationships in Enantioselective Catalysis: Past, Present, and Future.

Authors:  Andrew F Zahrt; Soumitra V Athavale; Scott E Denmark
Journal:  Chem Rev       Date:  2019-12-30       Impact factor: 60.622
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