Literature DB >> 26030059

Alkenyl carbonyl derivatives in enantioselective redox relay Heck reactions: accessing α,β-unsaturated systems.

Chun Zhang1, Celine B Santiago1, Lei Kou1, Matthew S Sigman1.   

Abstract

A highly enantioselective and site-selective Pd-catalyzed arylation of alkenes linked to carbonyl derivatives to yield α,β-unsaturated systems is reported. The high site selectivity is attributed to both a solvent effect and the polarized nature of the carbonyl group, both of which have been analyzed through multidimensional analysis tools. The reaction can be performed in an iterative fashion allowing for a diastereoselective installation of two aryl groups along an alkyl chain.

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Year:  2015        PMID： 26030059      PMCID： PMC4785797          DOI： 10.1021/jacs.5b04289

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


  40 in total

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3.  Mechanistic questions about the reaction of molecular oxygen with palladium in oxidase catalysis.

Authors:  Keith M Gligorich; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2006-10-13       Impact factor: 15.336

4.  The asymmetric Heck and related reactions.

Authors:  Dennis Mc Cartney; Patrick J Guiry
Journal:  Chem Soc Rev       Date:  2011-06-15       Impact factor: 54.564

5.  Palladium-catalyzed enantioselective Heck alkenylation of acyclic alkenols using a redox-relay strategy.

Authors:  Harshkumar H Patel; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-03-09       Impact factor: 15.419

6.  Asymmetric intermolecular boron Heck-type reactions via oxidative palladium(II) catalysis with chiral tridentate NHC-amidate-alkoxide ligands.

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Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

7.  Ligand-modulated palladium-catalyzed aerobic alcohol oxidations.

Authors:  Matthew S Sigman; David R Jensen
Journal:  Acc Chem Res       Date:  2006-03       Impact factor: 22.384

Review 8.  Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover.

Authors:  Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-28       Impact factor: 15.336

9.  Palladium-catalyzed oxidation of unsaturated hydrocarbons using molecular oxygen.

Authors:  Wanqing Wu; Huanfeng Jiang
Journal:  Acc Chem Res       Date:  2012-07-27       Impact factor: 22.384

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.  Parameterization of phosphine ligands reveals mechanistic pathways and predicts reaction outcomes.

Authors:  Zachary L Niemeyer; Anat Milo; David P Hickey; Matthew S Sigman
Journal:  Nat Chem       Date:  2016-05-16       Impact factor: 24.427

2.  Rate Profiling the Impact of Remote Functional Groups on the Redox-Relay Heck Reaction.

Authors:  Samantha L Kraus; Sean P Ross; Matthew S Sigman
Journal:  Org Lett       Date:  2021-03-12       Impact factor: 6.005

3.  Palladium-catalysed alkene chain-running isomerization.

Authors:  Andrew L Kocen; Maurice Brookhart; Olafs Daugulis
Journal:  Chem Commun (Camb)       Date:  2017-09-05       Impact factor: 6.222

4.  Enantioselective Dehydrogenative Heck Arylations of Trisubstituted Alkenes with Indoles to Construct Quaternary Stereocenters.

Authors:  Chun Zhang; Celine B Santiago; Jennifer M Crawford; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-12-10       Impact factor: 15.419

5.  11-Step Total Synthesis of Teleocidins B-1-B-4.

Authors:  Hugh Nakamura; Kosuke Yasui; Yuzuru Kanda; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-01-15       Impact factor: 15.419

6.  Enantiodivergent Fluorination of Allylic Alcohols: Data Set Design Reveals Structural Interplay between Achiral Directing Group and Chiral Anion.

Authors:  Andrew J Neel; Anat Milo; Matthew S Sigman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2016-03-11       Impact factor: 15.419

7.  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

8.  Intermolecular Heck Coupling with Hindered Alkenes Directed by Potassium Carboxylates.

Authors:  Tucker R Huffman; Yebin Wu; Alexis Emmerich; Ryan A Shenvi
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-25       Impact factor: 15.336

9.  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

10.  Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis.

Authors:  Jason S Chen; Andrew M Romine; Kin S Yang; Malkanthi K Karunananda; Keary M Engle
Journal:  ACS Catal       Date:  2019-07-02       Impact factor: 13.084
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