Literature DB >> 20526464

Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser's salt: One-pot preparation of diverse carbocyclic scaffolds.

Cara Cesario1, Marvin J Miller.   

Abstract

A formyl equivalent was generated in situ from Eschenmoser's salt in aqueous THF and was reacted with an allylindium species. Acylnitroso-derived hetero-Diels Alder adducts and related allyl acetates were shown to be substrates for Pd(0)/InI-mediated allylations of formaldehyde-related species to provide homoallylic alcohols. Hydroxymethyl groups were installed with regio- and diastereocontrol to provide relevant disubstituted carbocyclic scaffolds. Enantiopure anti-disubstituted cyclopentene products were prepared from a chiral allyl acetate.

Entities:  

Year:  2010        PMID： 20526464      PMCID： PMC2879704          DOI： 10.1016/j.tetlet.2010.04.007

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  11 in total

1.  Electrochemical Regeneration of Low-Valent Indium(I) Species as Catalysts for C-C Bond Formations This work was supported by the Deutsche Forschungsgemeinschaft. We thank Prof. W. Schnick, W. Wünschheim, and S. Rannabauer for the measurement of the Raman spectra.

Authors:  Gerhard Hilt; Konstantin I. Smolko
Journal:  Angew Chem Int Ed Engl       Date:  2001-09-17       Impact factor: 15.336

2.  Syntheses of carbocyclic aminonucleosides and (-)-epi-4'-carbocyclic puromycin: Application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations.

Authors:  Cara Cesario; Lawrence P Tardibono; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-06-09       Impact factor: 2.415

Review 3.  Synthesis and conformational and biological aspects of carbasugars.

Authors:  Odón Arjona; Ana M Gómez; J Cristóbal López; Joaquín Plumet
Journal:  Chem Rev       Date:  2007-05       Impact factor: 60.622

4.  An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen (1592U89).

Authors:  S M Daluge; M T Martin; B R Sickles; D A Livingston
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2000 Jan-Feb       Impact factor: 1.381

5.  Practical carbonyl-ene reactions of alpha-methylstyrenes with paraformaldehyde promoted by a combined system of boron trifluoride and molecular sieves 4A.

Authors:  Takahiro Okachi; Katsuhiko Fujimoto; Makoto Onaka
Journal:  Org Lett       Date:  2002-05-16       Impact factor: 6.005

6.  Application of phosphoramidate ProTide technology significantly improves antiviral potency of carbocyclic adenosine derivatives.

Authors:  Christopher McGuigan; Alshaimaa Hassan-Abdallah; Sheila Srinivasan; Yikang Wang; Adam Siddiqui; Susan M Daluge; Kristjan S Gudmundsson; Huiqiang Zhou; Ed W McLean; Jennifer P Peckham; Thimysta C Burnette; Harry Marr; Richard Hazen; Lynn D Condreay; Lance Johnson; Jan Balzarini
Journal:  J Med Chem       Date:  2006-11-30       Impact factor: 7.446

7.  Titanocene(III) chloride-mediated reductions of oxazines, hydroxamic acids, and N-hydroxy carbamates.

Authors:  Cara Cesario; Lawrence P Tardibono; Marvin J Miller
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354

8.  Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides.

Authors:  R Vince; M Hua
Journal:  J Med Chem       Date:  1990-01       Impact factor: 7.446

9.  Stereoselective total synthesis of racemic BCX-1812 (RWJ-270201) for the development of neuraminidase inhibitors as anti-influenza agents.

Authors:  Tomoko Mineno; Marvin J Miller
Journal:  J Org Chem       Date:  2003-08-22       Impact factor: 4.354

10.  Stereo- and regioselectivity of Pd(0)/InI-mediated allylic additions to aldehydes and ketones. In situ generation of allylindium(III) intermediates from N-acylnitroso Diels-Alder cycloadducts and 1-amino-4-acetoxycyclopentenes.

Authors:  Wenlin Lee; Kyung-Hee Kim; Matthew D Surman; Marvin J Miller
Journal:  J Org Chem       Date:  2003-01-10       Impact factor: 4.354
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  1 in total

1.  Syntheses of carbocyclic aminonucleosides and (-)-epi-4'-carbocyclic puromycin: Application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations.

Authors:  Cara Cesario; Lawrence P Tardibono; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-06-09       Impact factor: 2.415
  1 in total

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