Literature DB >> 28375015

Pd-Catalyzed Acyl C-O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines.

Christian A Malapit1, Donald R Caldwell1, Nicole Sassu1, Samuel Milbin1, Amy R Howell1.   

Abstract

A Pd-catalyzed ring-opening of β-lactones with various types of amines (primary, secondary, and aryl) to provide β-hydroxy amides with excellent selectivity toward acyl C-O bond cleavage is reported. The utility of this protocol is demonstrated in an asymmetric kinetic resolution providing enantioenriched α-methylene-β-lactones.

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Year:  2017        PMID： 28375015      PMCID： PMC5839468          DOI： 10.1021/acs.orglett.7b00494

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  16 in total

1.  Aromatic spiroketal bisphosphine ligands: palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts.

Authors:  Xiaoming Wang; Fanye Meng; Yan Wang; Zhaobin Han; Yong-Jun Chen; Li Liu; Zheng Wang; Kuiling Ding
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-15       Impact factor: 15.336

2.  Allylic carbon-carbon double bond directed Pd-catalyzed oxidative ortho-olefination of arenes.

Authors:  Parthasarathy Gandeepan; Chien-Hong Cheng
Journal:  J Am Chem Soc       Date:  2012-03-26       Impact factor: 15.419

3.  Pt-catalyzed rearrangement of oxaspirohexanes to 3-methylenetetrahydrofurans: scope and mechanism.

Authors:  Christian A Malapit; Sampada M Chitale; Meena S Thakur; Rosa Taboada; Amy R Howell
Journal:  J Org Chem       Date:  2015-05-06       Impact factor: 4.354

4.  Comparison of the reactivity of β-thiolactones and β-lactones toward ring-opening by thiols and amines.

Authors:  Amandine Noel; Bernard Delpech; David Crich
Journal:  Org Biomol Chem       Date:  2012-07-02       Impact factor: 3.876

5.  Spiroketal-based diphosphine ligands in Pd-catalyzed asymmetric allylic amination of Morita-Baylis-Hillman adducts: exceptionally high efficiency and new mechanism.

Authors:  Xiaoming Wang; Peihua Guo; Zhaobin Han; Xubin Wang; Zheng Wang; Kuiling Ding
Journal:  J Am Chem Soc       Date:  2013-12-24       Impact factor: 15.419

6.  Recent Applications of Oxetanes in the Synthesis of Heterocyclic Compounds.

Authors:  Christian A Malapit; Amy R Howell
Journal:  J Org Chem       Date:  2015-08-19       Impact factor: 4.354

7.  Palladium-Catalyzed Decarbonylative Cross-Coupling of Azinecarboxylates with Arylboronic Acids.

Authors:  Kei Muto; Taito Hatakeyama; Kenichiro Itami; Junichiro Yamaguchi
Journal:  Org Lett       Date:  2016-09-27       Impact factor: 6.005

8.  Pd-catalyzed π-chelation assisted ortho-C-H activation and annulation of allylarenes with internal alkynes.

Authors:  Parthasarathy Gandeepan; Chien-Hong Cheng
Journal:  Org Lett       Date:  2013-04-19       Impact factor: 6.005

9.  Catalytic cross-coupling reaction of esters with organoboron compounds and decarbonylative reduction of esters with HCOONH4: a new route to acyl transition metal complexes through the cleavage of acyl-oxygen bonds in esters.

Authors:  Hiroto Tatamidani; Kazuhiko Yokota; Fumitoshi Kakiuchi; Naoto Chatani
Journal:  J Org Chem       Date:  2004-08-20       Impact factor: 4.354

10.  Decarbonylative organoboron cross-coupling of esters by nickel catalysis.

Authors:  Kei Muto; Junichiro Yamaguchi; Djamaladdin G Musaev; Kenichiro Itami
Journal:  Nat Commun       Date:  2015-06-29       Impact factor: 14.919
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  5 in total

1.  Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted β-Lactones.

Authors:  Christian A Malapit; Irungu K Luvaga; Donald R Caldwell; Nicholas K Schipper; Amy R Howell
Journal:  Org Lett       Date:  2017-08-15       Impact factor: 6.005

2.  Nickel-Catalyzed Decarbonylative Amination of Carboxylic Acid Esters.

Authors:  Christian A Malapit; Margarida Borrell; Michael W Milbauer; Conor E Brigham; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2020-03-24       Impact factor: 15.419

3.  Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters.

Authors:  Amira H Dardir; Patrick R Melvin; Ryan M Davis; Nilay Hazari; Megan Mohadjer Beromi
Journal:  J Org Chem       Date:  2017-12-12       Impact factor: 4.354

4.  Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones.

Authors:  Yao Ge; Fei Ye; Jiawang Liu; Ji Yang; Anke Spannenberg; Haijun Jiao; Ralf Jackstell; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-17       Impact factor: 15.336

5.  α-Methylene-β-Lactone Scaffold for Developing Chemical Probes at the Two Ends of the Selectivity Spectrum.

Authors:  Lei Wang; Louis P Riel; Bekim Bajrami; Bin Deng; Amy R Howell; Xudong Yao
Journal:  Chembiochem       Date:  2020-11-11       Impact factor: 3.164
  5 in total

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