Literature DB >> 20687578

Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.

Robert E Kyne1, Michael C Ryan, Laura T Kliman, James P Morken.   

Abstract

Addition of nitrosobenzene to pinacol allylboronates leads to oxidation of the organoboron with concomitant rearrangement of the substrate alkene. This reaction appears to proceed by allylboration of the nitroso group in analogy to carbonyl and imine allylation reactions. Remarkably, the N-O bond is cleaved during the reaction such that simple alcohols are the final reaction product.

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Year:  2010        PMID： 20687578      PMCID： PMC2929327          DOI： 10.1021/ol101472k

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


  20 in total

1.  Unusual diboration of allenes catalyzed by palladium complexes and organic iodides: a new efficient route to biboronic compounds.

Authors:  F Y Yang; C H Cheng
Journal:  J Am Chem Soc       Date:  2001-01-31       Impact factor: 15.419

2.  Sequential Pd-catalyzed asymmetric allene diboration/alpha-aminoallylation.

Authors:  Joshua D Sieber; James P Morken
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

3.  Catalytic conjugate addition of allyl groups to styryl-activated enones.

Authors:  Joshua D Sieber; Shubin Liu; James P Morken
Journal:  J Am Chem Soc       Date:  2007-02-01       Impact factor: 15.419

4.  Direct amino acid-catalyzed asymmetric desymmetrization of meso-compounds: tandem aminoxylation/O-N bond heterolysis reactions.

Authors:  Dhevalapally B Ramachary; Carlos F Barbas
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

5.  Modular asymmetric synthesis of 1,2-diols by single-pot allene diboration/hydroboration/cross-coupling.

Authors:  Nicholas F Pelz; James P Morken
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

6.  Platinum-catalyzed tandem diboration/asymmetric allylboration: access to nonracemic functionalized 1,3-diols.

Authors:  Jeremy B Morgan; James P Morken
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

7.  Palladium(0) versus nickel(0) catalysis in selective functional-group-tolerant sp(3)-sp(3) carbon-carbon bond formations.

Authors:  Emmanuel Ferrer Flegeau; Uwe Schneider; Shū Kobayashi
Journal:  Chemistry       Date:  2009-11-16       Impact factor: 5.236

8.  Iron-catalyzed 1,4-hydroboration of 1,3-dienes.

Authors:  Jessica Y Wu; Benoît Moreau; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

9.  Enantioselective tandem O-nitroso Aldol/Michael reaction.

Authors:  Yuhei Yamamoto; Norie Momiyama; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2004-05-19       Impact factor: 15.419

10.  The direct and enantioselective organocatalytic alpha-oxidation of aldehydes.

Authors:  Sean P Brown; Michael P Brochu; Christopher J Sinz; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2003-09-10       Impact factor: 15.419
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  7 in total

1.  Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

Authors:  Xiben Li; Fanke Meng; Sebastian Torker; Ying Shi; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-20       Impact factor: 15.336

2.  Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents.

Authors:  Emma K Edelstein; Sheila Namirembe; James P Morken
Journal:  J Am Chem Soc       Date:  2017-03-29       Impact factor: 15.419

3.  Synthesis and Utility of Dihydropyridine Boronic Esters.

Authors:  Santanu Panda; Aaron Coffin; Q Nhu Nguyen; Dean J Tantillo; Joseph M Ready
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

4.  Enantiomerically enriched tris(boronates): readily accessible conjunctive reagents for asymmetric synthesis.

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  J Am Chem Soc       Date:  2014-11-11       Impact factor: 15.419

5.  3-Chloro-1-lithiopropene, a functional organolithium reagent, and its reactions with alkylboronates to give 3-alkylprop-1-en-3-ols.

Authors:  Keith Smith; Mark C Elliott; D Heulyn Jones
Journal:  J Org Chem       Date:  2013-09-11       Impact factor: 4.354

6.  Nonracemic allylic boronates through enantiotopic-group-selective cross-coupling of geminal bis(boronates) and vinyl halides.

Authors:  Bowman Potter; Adam A Szymaniak; Emma K Edelstein; James P Morken
Journal:  J Am Chem Soc       Date:  2014-12-15       Impact factor: 15.419

7.  Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles.

Authors:  Cristina García-Ruiz; Jack L-Y Chen; Christopher Sandford; Kathryn Feeney; Paula Lorenzo; Guillaume Berionni; Herbert Mayr; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2017-10-20       Impact factor: 15.419
  7 in total

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