Literature DB >> 16986971

Ring expansion/homologation--aldehyde condensation cascade using tert-trihalomethylcarbinols.

J R Falck1, Anyu He, L Manmohan Reddy, Abhijit Kundu, Deb K Barma, A Bandyopadhyay, Sukanta Kamila, Radha Akella, Romain Bejot, Charles Mioskowski.   

Abstract

Treatment of cyclic tert-trihalomethylcarbinols with CrCl(2) in THF/HMPA in the presence of aryl or aliphatic aldehydes initiates a cascade sequence of one carbon ring expansion-olefination affording conjugated exocyclic ketones. Acyclic tert-trihalomethylcarbinols undergo a comparable cascade of one carbon homologation-olefination.

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Year:  2006        PMID： 16986971      PMCID： PMC2517229          DOI： 10.1021/ol061953q

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


  4 in total

1.  A practical preparation of terminal alkynes from aldehydes.

Authors:  Z Wang; S Campagna; K Yang; G Xu; M E Pierce; J M Fortunak; P N Confalone
Journal:  J Org Chem       Date:  2000-03-24       Impact factor: 4.354

2.  Amidine-promoted addition of chloroform to carbonyl compounds

Authors: 
Journal:  J Org Chem       Date:  2000-10-20       Impact factor: 4.354

3.  Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride.

Authors:  Romain Bejot; Steve Tisserand; L Manmohan Reddy; Deb K Barma; Rachid Baati; J R Falck; Charles Mioskowski
Journal:  Angew Chem Int Ed Engl       Date:  2005-03-18       Impact factor: 15.336

4.  Selective synthesis of alpha,beta-unsaturated ketones by dibutyltin dimethoxide-catalyzed condensation of aldehydes with alkenyl trichloroacetates.

Authors:  Akira Yanagisawa; Riku Goudu; Takayoshi Arai
Journal:  Org Lett       Date:  2004-11-11       Impact factor: 6.005
  4 in total
  2 in total

1.  Cascade synthesis of (E)-2-alkylidenecyclobutanols.

Authors:  J R Falck; Anish Bandyopadhyay; Narender Puli; Abhijit Kundu; L Manmohan Reddy; Deb K Barma; Anyu He; Hongming Zhang; Dhurke Kashinath; Rachid Baati
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

2.  Petromylidenes A⁻C: 2-Alkylidene Bile Salt Derivatives Isolated from Sea Lamprey (Petromyzon marinus).

Authors:  Ke Li; Anne M Scott; Skye D Fissette; Tyler J Buchinger; Joseph J Riedy; Weiming Li
Journal:  Mar Drugs       Date:  2018-09-01       Impact factor: 5.118
  2 in total

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