Literature DB >> 22506671

Palladium-catalyzed asymmetric allylic alkylation of electron-deficient pyrroles with meso electrophiles.

Barry M Trost1, Maksim Osipov, Guangbin Dong.   

Abstract

Pyrroles can serve as competent nucleophiles with meso electrophiles in the Pd-catalyzed asymmetric allylic alkylation. The products from this transformation were obtained as a single regio- and diastereomer in high yield and enantiopurity. A nitropyrrole-containing nucleoside analogue was synthesized in seven steps to demonstrate the synthetic utility of this transformation.

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Year:  2012        PMID： 22506671      PMCID： PMC3407807          DOI： 10.1021/ol3006584

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


  20 in total

1.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

Review 2.  L-nucleoside enantiomers as antivirals drugs: a mini-review.

Authors:  Christophe Mathé; Gilles Gosselin
Journal:  Antiviral Res       Date:  2006-05-23       Impact factor: 5.970

3.  Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model.

Authors:  Barry M Trost; Michelle R Machacek; Aaron Aponick
Journal:  Acc Chem Res       Date:  2006-10       Impact factor: 22.384

4.  New class of nucleophiles for palladium-catalyzed asymmetric allylic alkylation. Total synthesis of agelastatin A.

Authors:  Barry M Trost; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2006-05-10       Impact factor: 15.419

5.  Palladium-catalyzed dynamic kinetic asymmetric transformations of vinyl aziridines with nitrogen heterocycles: rapid access to biologically active pyrroles and indoles.

Authors:  Barry M Trost; Maksim Osipov; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

6.  Strategy for employing unstabilized nucleophiles in palladium-catalyzed asymmetric allylic alkylations.

Authors:  Barry M Trost; David A Thaisrivongs
Journal:  J Am Chem Soc       Date:  2008-10-01       Impact factor: 15.419

7.  Growth inhibition and induction of cellular differentiation of human myeloid leukemia cells in culture by carbamoyl congeners of ribavirin.

Authors:  Y S Sanghvi; B K Bhattacharya; G D Kini; S S Matsumoto; S B Larson; W B Jolley; R K Robins; G R Revankar
Journal:  J Med Chem       Date:  1990-01       Impact factor: 7.446

8.  A stereodivergent strategy to both product enantiomers from the same enantiomer of a stereoinducing catalyst: agelastatin A.

Authors:  Barry M Trost; Guangbin Dong
Journal:  Chemistry       Date:  2009-07-13       Impact factor: 5.236

9.  Structure-based rationale for selectivity in the asymmetric allylic alkylation of cycloalkenyl esters employing the Trost 'Standard Ligand' (TSL): isolation, analysis and alkylation of the monomeric form of the cationic eta(3)-cyclohexenyl complex [(eta(3)-c-C6H9)Pd(TSL)]+.

Authors:  Craig P Butts; Emane Filali; Guy C Lloyd-Jones; Per-Ola Norrby; David A Sale; York Schramm
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

10.  Synthesis and antiviral evaluation of a mutagenic and non-hydrogen bonding ribonucleoside analogue: 1-beta-D-Ribofuranosyl-3-nitropyrrole.

Authors:  Daniel A Harki; Jason D Graci; Victoria S Korneeva; Saikat Kumar B Ghosh; Zhi Hong; Craig E Cameron; Blake R Peterson
Journal:  Biochemistry       Date:  2002-07-23       Impact factor: 3.162
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  1 in total

1.  Metal Catalyzed Allylic Alkylation: Its Development in the Trost Laboratories.

Authors:  Barry M Trost
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457
  1 in total

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