Literature DB >> 20455553

Efficient diacetoxylation of alkenes via Pd(II)/Pd(IV) process with peracetic acid and acetic anhydride.

Chan Pil Park1, Joo Ho Lee, Kyung Soo Yoo, Kyung Woon Jung.   

Abstract

A palladium-catalyzed diacetoxylation of alkenes in the presence of peracetic acid and acetic anhydride was developed to produce diacetates efficiently and diastereoselectively. Due to its mild conditions, this method was suitable for a broad range of substrates encompassing conjugated and nonconjugated olefins.

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Year:  2010        PMID： 20455553      PMCID： PMC2880612          DOI： 10.1021/ol1001686

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


  11 in total

1.  Construction of tetrahydrofurans by PdII/PdIV-catalyzed aminooxygenation of alkenes.

Authors:  Lopa V Desai; Melanie S Sanford
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Palladium-catalyzed olefin dioxygenation.

Authors:  Yang Li; Datong Song; Vy M Dong
Journal:  J Am Chem Soc       Date:  2008-02-19       Impact factor: 15.419

3.  Mechanistic insights into the palladiumII-catalyzed hydroxyalkoxylation of 2-allylphenols.

Authors:  Emilie Thiery; Carole Chevrin; Jean Le Bras; Dominique Harakat; Jacques Muzart
Journal:  J Org Chem       Date:  2007-02-03       Impact factor: 4.354

4.  Palladium(II)-catalyzed aerobic dialkoxylation of styrenes: a profound influence of an o-phenol.

Authors:  Mitchell J Schultz; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2006-02-08       Impact factor: 15.419

5.  New osmium-based reagent for the dihydroxylation of alkenes.

Authors:  Timothy J Donohoe; Robert M Harris; Sam Butterworth; Jeremy N Burrows; Andrew Cowley; Jeremy S Parker
Journal:  J Org Chem       Date:  2006-06-09       Impact factor: 4.354

6.  Palladium(II)-catalyzed enantioselective aerobic dialkoxylation of 2-propenyl phenols: a pronounced effect of copper additives on enantioselectivity.

Authors:  Yang Zhang; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2007-02-14       Impact factor: 15.419

7.  De novo enantioselective syntheses of galacto-sugars and deoxy sugars via the iterative dihydroxylation of dienoate.

Authors:  Md Moinuddin Ahmed; Bryan P Berry; Thomas J Hunter; Dennis J Tomcik; George A O'Doherty
Journal:  Org Lett       Date:  2005-02-17       Impact factor: 6.005

8.  Palladium-catalyzed diacetoxylation of alkenes with molecular oxygen as sole oxidant.

Authors:  Azhong Wang; Huanfeng Jiang; Huoji Chen
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419

9.  Mechanistic approaches to palladium-catalyzed alkene difunctionalization reactions.

Authors:  Katrina H Jensen; Matthew S Sigman
Journal:  Org Biomol Chem       Date:  2008-10-09       Impact factor: 3.876

10.  A highly selective catalytic method for the oxidative functionalization of C-H bonds.

Authors:  Allison R Dick; Kami L Hull; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2004-03-03       Impact factor: 15.419
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  7 in total

1.  Palladium(II)-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives.

Authors:  Ranjan Jana; Tejas P Pathak; Katrina H Jensen; Matthew S Sigman
Journal:  Org Lett       Date:  2012-08-08       Impact factor: 6.005

2.  Aerobic palladium-catalyzed dioxygenation of alkenes enabled by catalytic nitrite.

Authors:  Zachary K Wickens; Pablo E Guzmán; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-06       Impact factor: 15.336

3.  Advancing the mechanistic understanding of an enantioselective palladium-catalyzed alkene difunctionalization reaction.

Authors:  Katrina H Jensen; Jonathan D Webb; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2010-11-17       Impact factor: 15.419

4.  Anti-Markovnikov hydroalkylation of allylic amine derivatives via a palladium-catalyzed reductive cross-coupling reaction.

Authors:  Ryan J DeLuca; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-07-11       Impact factor: 15.419

5.  Asymmetric chiral ligand-directed alkene dioxygenation.

Authors:  Sharon R Neufeldt; Melanie S Sanford
Journal:  Org Lett       Date:  2012-12-18       Impact factor: 6.005

6.  Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy.

Authors:  Huili Liu; Kuan Zheng; Xiang Lu; Xiaoxia Wang; Ran Hong
Journal:  Beilstein J Org Chem       Date:  2013-05-23       Impact factor: 2.883

7.  A highly productive, whole-cell DERA chemoenzymatic process for production of key lactonized side-chain intermediates in statin synthesis.

Authors:  Matej Ošlaj; Jérôme Cluzeau; Damir Orkić; Gregor Kopitar; Peter Mrak; Zdenko Casar
Journal:  PLoS One       Date:  2013-05-07       Impact factor: 3.240
  7 in total

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