Literature DB >> 27571167

Palladium-Catalyzed Enantioselective Redox-Relay Heck Arylation of 1,1-Disubstituted Homoallylic Alcohols.

Zhi-Min Chen1, Margaret J Hilton1, Matthew S Sigman1.   

Abstract

An enantioselective redox-relay oxidative Heck arylation of 1,1-disubstituted alkenes to construct β-stereocenters was developed using a new pyridyl-oxazoline ligand. Various 1,2-diaryl carbonyl compounds were readily obtained in moderate yield and good to excellent enantioselectivity. Additionally, analysis of the reaction outcomes using multidimensional correlations revealed that enantioselectivity is tied to specific electronic features of the 1,1-disubstituted alkenol and the extent of polarizability of the ligand.

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Year:  2016        PMID: 27571167      PMCID: PMC5039009          DOI: 10.1021/jacs.6b06994

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


  44 in total

1.  Towards organocatalytic polyketide synthases with diverse electrophile scope: trifluoroethyl thioesters as nucleophiles in organocatalytic Michael reactions and beyond.

Authors:  Diego A Alonso; Shinji Kitagaki; Naoto Utsumi; Carlos F Barbas
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  3D-QSAR studies of 1,2-diaryl-1H-benzimidazole derivatives as JNK3 inhibitors with protective effects in neuronal cells.

Authors:  Mi-Hyun Kim; Jae-Sang Ryu; Jung-Mi Hah
Journal:  Bioorg Med Chem Lett       Date:  2013-01-29       Impact factor: 2.823

3.  Face-to-face arene-arene binding energies: dominated by dispersion but predicted by electrostatic and dispersion/polarizability substituent constants.

Authors:  Michelle Watt; Laura K E Hardebeck; Charles C Kirkpatrick; Michael Lewis
Journal:  J Am Chem Soc       Date:  2011-03-01       Impact factor: 15.419

4.  Ligand-accelerated Pd-catalyzed ketone γ-arylation via C-C cleavage with aryl chlorides.

Authors:  Asraa Ziadi; Ruben Martin
Journal:  Org Lett       Date:  2012-02-14       Impact factor: 6.005

5.  A highly selective and general palladium catalyst for the oxidative Heck reaction of electronically nonbiased olefins.

Authors:  Erik W Werner; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

6.  Synthesis and Biological Evaluations of 1,2-Diaryl Pyrroles as Analogues of Combretastatin A-4.

Authors:  Jun Sun; Lei Chen; Chunjiang Liu; Zhan Wang; Daiying Zuo; Jiatong Pan; Huan Qi; Kai Bao; Yingliang Wu; Weige Zhang
Journal:  Chem Biol Drug Des       Date:  2015-09-25       Impact factor: 2.817

7.  Catalytic asymmetric cross-couplings of racemic alpha-bromoketones with arylzinc reagents.

Authors:  Pamela M Lundin; Jorge Esquivias; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Rh-catalyzed addition of β-carbonyl pinacol alkylboronates to aldehydes: asymmetric synthesis of γ-butyrolactones.

Authors:  Changwan Zhang; Jaesook Yun
Journal:  Org Lett       Date:  2013-06-17       Impact factor: 6.005

9.  Diarylation of alkenes by a Cu-catalyzed migratory insertion/cross-coupling cascade.

Authors:  Wei You; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2014-10-10       Impact factor: 15.419

10.  Mechanism, reactivity, and selectivity in palladium-catalyzed redox-relay Heck arylations of alkenyl alcohols.

Authors:  Liping Xu; Margaret J Hilton; Xinhao Zhang; Per-Ola Norrby; Yun-Dong Wu; Matthew S Sigman; Olaf Wiest
Journal:  J Am Chem Soc       Date:  2014-01-22       Impact factor: 15.419

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  22 in total

1.  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

2.  Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis.

Authors:  Wei Liu; Siraj Z Ali; Stephen E Ammann; M Christina White
Journal:  J Am Chem Soc       Date:  2018-08-17       Impact factor: 15.419

3.  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

4.  Palladium-Catalyzed Enantioselective Redox-Relay Heck Alkynylation of Alkenols To Access Propargylic Stereocenters.

Authors:  Zhi-Min Chen; Christine S Nervig; Ryan J DeLuca; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-03       Impact factor: 15.336

5.  Transition State Force Field for the Asymmetric Redox-Relay Heck Reaction.

Authors:  Anthony R Rosales; Sean P Ross; Paul Helquist; Per-Ola Norrby; Matthew S Sigman; Olaf Wiest
Journal:  J Am Chem Soc       Date:  2020-05-14       Impact factor: 15.419

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

Authors:  Eiji Yamamoto; Margaret J Hilton; Manuel Orlandi; Vaneet Saini; F Dean Toste; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-11-30       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.  A Transient-Directing-Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes.

Authors:  Lucas J Oxtoby; Zi-Qi Li; Van T Tran; Tuğçe G Erbay; Ruohan Deng; Peng Liu; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-07       Impact factor: 15.336

Review 9.  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

10.  Development and Mechanistic Interrogation of Interrupted Chain-Walking in the Enantioselective Relay Heck Reaction.

Authors:  Sean P Ross; Ajara A Rahman; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2020-05-29       Impact factor: 15.419

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