Literature DB >> 34421135

Tandem Homologation-Acylation Chemistry: Single and Double Homologation.

Carley S Henderson1, Jennifer R Mazzone1, Amanda M Moore1, Charles K Zercher1.   

Abstract

Treatment of β-dicarbonyls with the Furakawa-variant of the Simmons-Smith reagent results in homologation and production of an intermediate zinc enolate. Treatment of the enolate with various acylating agents generate products with both γ-dicarbonyl functionality and β-dicarbonyl functionality. In situ exposure of the acylated product to additional zinc carbenoid effects a second regiospecific homologation reaction.

Entities:  

Year:  2021        PMID： 34421135      PMCID： PMC8372754          DOI： 10.1016/j.tet.2021.132223

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.388


  10 in total

1.  Carbamoylation of aryl halides by molybdenum or tungsten carbonyl amine complexes.

Authors:  Wei Ren; Motoki Yamane
Journal:  J Org Chem       Date:  2010-05-07       Impact factor: 4.354

2.  Tandem chain extension-homoenolate formation: the formation of alpha-methylated-gamma-keto esters.

Authors:  R Hilgenkamp; C K Zercher
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

3.  Solution phase synthesis of a library of tetrasubstituted pyrrole amides.

Authors:  Ivana Bianchi; Roberto Forlani; Giacomo Minetto; Ilaria Peretto; Nickolas Regalia; Maurizio Taddei; Luca F Raveglia
Journal:  J Comb Chem       Date:  2006 Jul-Aug

4.  Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate.

Authors:  S Lai; C K Zercher; J P Jasinski; S N Reid; R J Staples
Journal:  Org Lett       Date:  2001-12-27       Impact factor: 6.005

5.  Zinc-mediated chain extension of beta-keto phosphonates

Authors: 
Journal:  J Org Chem       Date:  2000-09-08       Impact factor: 4.354

6.  Syntheses of papyracillic acids: application of the tandem chain extension-acylation reaction.

Authors:  Jennifer R Mazzone; Charles K Zercher
Journal:  J Org Chem       Date:  2012-10-05       Impact factor: 4.354

7.  Synthesis of beta-dicarbonyl compounds using 1-acylbenzotriazoles as regioselective C-acylating reagents

Authors: 
Journal:  J Org Chem       Date:  2000-06-16       Impact factor: 4.354

8.  A new facile approach to the synthesis of 3-methylthio-substituted furans, pyrroles, thiophenes, and related derivatives.

Authors:  Guodong Yin; Zihua Wang; Aihua Chen; Meng Gao; Anxin Wu; Yuanjiang Pan
Journal:  J Org Chem       Date:  2008-03-20       Impact factor: 4.354

9.  Zinc carbenoid-mediated chain extension: preparation of alpha,beta-unsaturated-gamma-keto esters and amides.

Authors:  Matthew D Ronsheim; Charles K Zercher
Journal:  J Org Chem       Date:  2003-05-30       Impact factor: 4.354

10.  Tandem chain extension-Mannich reaction: an approach to β-proline derivatives.

Authors:  Alexander M Jacobine; Angela L A Puchlopek; Charles K Zercher; Jon B Briggs; Jerry P Jasinski; Raymond J Butcher
Journal:  Tetrahedron       Date:  2012-07-17       Impact factor: 2.457
  10 in total

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