Literature DB >> 27754648

Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

Scott A Shuler1, Guoyin Yin1, Sarah B Krause1, Caroline M Vesper1, Donald A Watson1.   

Abstract

The preparation of unsaturated secondary lactams via the palladium-catalyzed cyclization of O-phenyl hydroxamates onto a pendent alkene is reported. This method provides rapid access to a broad range of lactams that are widely useful building blocks in alkaloid synthesis. Mechanistic studies support an aza-Heck-type pathway.

Entities:  

Year:  2016        PMID： 27754648      PMCID： PMC5395365          DOI： 10.1021/jacs.6b08932

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


  55 in total

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3.  Influence of catalyst structure and reaction conditions on anti- versus syn-aminopalladation pathways in Pd-catalyzed alkene carboamination reactions of N-allylsulfamides.

Authors:  Ryan M Fornwald; Jonathan A Fritz; John P Wolfe
Journal:  Chemistry       Date:  2014-06-17       Impact factor: 5.236

4.  Mechanistic studies of Wacker-type amidocyclization of alkenes catalyzed by (IMes)Pd(TFA)2(H2O): kinetic and stereochemical implications of proton transfer.

Authors:  Xuan Ye; Paul B White; Shannon S Stahl
Journal:  J Org Chem       Date:  2012-11-30       Impact factor: 4.354

5.  Umpolung amination: nickel-catalyzed coupling reactions of N,N-dialkyl-N-chloroamines with diorganozinc reagents.

Authors:  Timothy J Barker; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

6.  Palladium catalyzed cyclizations of oxime esters with 1,2-disubstituted alkenes: synthesis of dihydropyrroles.

Authors:  Nicholas J Race; John F Bower
Journal:  Org Lett       Date:  2013-08-27       Impact factor: 6.005

Review 7.  C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents.

Authors:  Egle M Beccalli; Gianluigi Broggini; Michela Martinelli; Silvia Sottocornola
Journal:  Chem Rev       Date:  2007-11-01       Impact factor: 60.622

8.  Chiral cyclopentadienyl ligands as stereocontrolling element in asymmetric C-H functionalization.

Authors:  Baihua Ye; Nicolai Cramer
Journal:  Science       Date:  2012-10-26       Impact factor: 47.728

9.  Regio- and enantiospecific rhodium-catalyzed allylic substitution with an acyl anion equivalent.

Authors:  P Andrew Evans; Samuel Oliver
Journal:  Org Lett       Date:  2013-11-01       Impact factor: 6.005

10.  Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions.

Authors:  Vasily Kotov; Christopher C Scarborough; Shannon S Stahl
Journal:  Inorg Chem       Date:  2007-03-19       Impact factor: 5.165
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  10 in total

Review 1.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

2.  Synthesis of Indolines and Derivatives by Aza-Heck Cyclization.

Authors:  Feiyang Xu; Katerina M Korch; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-13       Impact factor: 15.336

3.  Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Org Lett       Date:  2021-08-30       Impact factor: 6.072

4.  Radical Aza-Heck Cyclization of Imidates via Energy Transfer, Electron Transfer, and Cobalt Catalysis.

Authors:  Allen F Prusinowski; Henry C Sise; Taylor N Bednar; David A Nagib
Journal:  ACS Catal       Date:  2022-03-28       Impact factor: 13.700

5.  Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D: Development of a Stereodivergent Strategy.

Authors:  You-Chen Lin; Aubert Ribaucourt; Yasamin Moazami; Joshua G Pierce
Journal:  J Am Chem Soc       Date:  2020-05-12       Impact factor: 15.419

6.  A Facile Direct Route to N-(Un)substituted Lactams by Cycloamination of Oxocarboxylic Acids without External Hydrogen.

Authors:  Hu Li; Hongguo Wu; Heng Zhang; Yaqiong Su; Song Yang; Emiel J M Hensen
Journal:  ChemSusChem       Date:  2019-07-17       Impact factor: 8.928

7.  Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades.

Authors:  Benjamin T Jones; Javier García-Cárceles; Lewis Caiger; Ian R Hazelden; Richard J Lewis; Thomas Langer; John F Bower
Journal:  J Am Chem Soc       Date:  2021-09-21       Impact factor: 15.419

8.  Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp3)-H Functionalization Cascades.

Authors:  Changcheng Jing; Benjamin T Jones; Ross J Adams; John F Bower
Journal:  J Am Chem Soc       Date:  2022-09-09       Impact factor: 16.383

9.  Tandem aza-Heck Suzuki and carbonylation reactions of O-phenyl hydroxamic ethers: complex lactams via carboamination.

Authors:  Run-Duo Gao; Scott A Shuler; Donald A Watson
Journal:  Chem Sci       Date:  2021-05-27       Impact factor: 9.825

Review 10.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823
  10 in total

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