Literature DB >> 10930249

Palladium-catalyzed intramolecular coupling of vinyl halides and ketone enolates. Synthesis Of bridged azabicyclic compounds

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Abstract

The palladium-mediated intramolecular coupling of amino-tethered vinyl halides and ketone enolates is a useful methodology for the synthesis of nitrogen heterocycles and constitutes a new synthetic entry to the 2-azabicyclo[3.3.1]nonane framework. A study about the reaction conditions and the scope of the process is reported.

Entities:  

Year:  2000        PMID： 10930249     DOI： 10.1021/ol005973i

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


  9 in total

1.  Palladium-Catalyzed Selective α-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides.

Authors:  Xiaodong Yang; Byeong-Seon Kim; Minyan Li; Patrick J Walsh
Journal:  Org Lett       Date:  2016-05-10       Impact factor: 6.005

2.  Total synthesis of (+/-)-strychnine via a [4 + 2]-cycloaddition/rearrangement cascade.

Authors:  Hongjun Zhang; Jutatip Boonsombat; Albert Padwa
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

3.  Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-Na -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine.

Authors:  Michael Rajesh Stephen; M Toufiqur Rahman; V V N Phani Babu Tiruveedhula; German O Fonseca; Jeffrey R Deschamps; James M Cook
Journal:  Chemistry       Date:  2017-10-18       Impact factor: 5.236

4.  Enantiospecific total synthesis of the important biogenetic intermediates along the ajmaline pathway, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epivellosimine and macusine A.

Authors:  Wenyuan Yin; M Shahjahan Kabir; Zhijian Wang; Sundari K Rallapalli; Jun Ma; James M Cook
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

5.  Transition-metal-free chemo- and regioselective vinylation of azaallyls.

Authors:  Minyan Li; Osvaldo Gutierrez; Simon Berritt; Ana Pascual-Escudero; Ahmet Yeşilçimen; Xiaodong Yang; Javier Adrio; Georgia Huang; Eiko Nakamaru-Ogiso; Marisa C Kozlowski; Patrick J Walsh
Journal:  Nat Chem       Date:  2017-04-17       Impact factor: 24.427

6.  A Catalytic Intermolecular Formal Ene Reaction between Ketone-Derived Silyl Enol Ethers and Alkynes.

Authors:  Stephen D Holmbo; Nicole A Godfrey; Joshua J Hirner; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2016-09-16       Impact factor: 15.419

7.  Total synthesis of the strychnos alkaloid (+)-minfiensine: tandem enantioselective intramolecular Heck-iminium ion cyclization.

Authors:  Amy B Dounay; Philip G Humphreys; Larry E Overman; Aaron D Wrobleski
Journal:  J Am Chem Soc       Date:  2008-02-28       Impact factor: 15.419

8.  Regio- and stereospecific rhodium-catalyzed allylic alkylation with an acyl anion equivalent: an approach to acyclic α-ternary β,γ-unsaturated aryl ketones.

Authors:  Ben W H Turnbull; Jungha Chae; Samuel Oliver; P Andrew Evans
Journal:  Chem Sci       Date:  2017-03-31       Impact factor: 9.825

9.  Total synthesis of the akuammiline alkaloid picrinine.

Authors:  Joel M Smith; Jesus Moreno; Ben W Boal; Neil K Garg
Journal:  J Am Chem Soc       Date:  2014-03-12       Impact factor: 15.419
  9 in total

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