Literature DB >> 18570376

Intermolecular hydroamination of allenes with N-unsubstituted carbamates catalyzed by a gold(I) N-heterocyclic carbene complex.

Robert E Kinder1, Zhibin Zhang, Ross A Widenhoefer.   

Abstract

Reaction of 2,3-pentadienyl benzoate with benzyl carbamate catalyzed by a 1:1 mixture of (NHC)AuCl and AgOTf in dioxane at 23 degrees C for 5 h led to isolation of (E)-4-(benzyloxycarbonylamino)-2-pentenyl benzoate in 84% yield as a single regio- and diastereomer. Gold(I)-catalyzed hydroamination was effective for a number of N-unsubstituted carbamates and a range of substituted allenes.

Entities:  

Mesh：

Substances：

Year:  2008        PMID： 18570376      PMCID： PMC2727634          DOI： 10.1021/ol8010858

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


  38 in total

1.  Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes.

Authors:  Zhibin Zhang; Christopher F Bender; Ross A Widenhoefer
Journal:  J Am Chem Soc       Date:  2007-10-30       Impact factor: 15.419

2.  Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis.

Authors:  Sean A Reed; M Christina White
Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

3.  Bifunctional organocatalysts for enantioselective aza-Morita-Baylis-Hillman reaction.

Authors:  Katsuya Matsui; Shinobu Takizawa; Hiroaki Sasai
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

4.  Gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols: highly efficient synthesis of fully substituted dihydrofurans and furans.

Authors:  Yuanhong Liu; Feijie Song; Zhiquan Song; Meina Liu; Bin Yan
Journal:  Org Lett       Date:  2005-11-24       Impact factor: 6.005

5.  Practical, highly active, and enantioselective ferrocenyl-imidazoline palladacycle catalysts (FIPs) for the aza-Claisen rearrangement of N-para-methoxyphenyl trifluoroacetimidates.

Authors:  Matthias E Weiss; Daniel F Fischer; Zhuo-Qun Xin; Sascha Jautze; W Bernd Schweizer; René Peters
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-25       Impact factor: 15.336

6.  Gold catalysis: mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects.

Authors:  A Stephen K Hashmi; Jan P Weyrauch; Wolfgang Frey; Jan W Bats
Journal:  Org Lett       Date:  2004-11-11       Impact factor: 6.005

7.  Golden opportunities in natural product synthesis: first total synthesis of (-)-isocyclocapitelline and (-)-isochrysotricine by gold-catalyzed allene cycloisomerization.

Authors:  Frank Volz; Norbert Krause
Journal:  Org Biomol Chem       Date:  2007-04-16       Impact factor: 3.876

8.  The reaction mechanism of the hydroamination of alkenes catalyzed by gold(I)-phosphine: the role of the counterion and the N-nucleophile substituents in the proton-transfer step.

Authors:  Gábor Kovács; Gregori Ujaque; Agustí Lledós
Journal:  J Am Chem Soc       Date:  2008-01-01       Impact factor: 15.419

9.  Use of group 4 bis(sulfonamido) complexes in the intramolecular hydroamination of alkynes and allenes.

Authors:  Lutz Ackermann; Robert G Bergman; Rebecca N Loy
Journal:  J Am Chem Soc       Date:  2003-10-01       Impact factor: 15.419

10.  Toward a synthetically useful stereoselective C-H amination of hydrocarbons.

Authors:  Chungen Liang; Florence Collet; Fabien Robert-Peillard; Paul Müller; Robert H Dodd; Philippe Dauban
Journal:  J Am Chem Soc       Date:  2007-12-12       Impact factor: 15.419
View more
  16 in total

1.  Gold(I)-Catalyzed Intramolecular Hydroamination of N-Allylic,N'-Aryl Ureas to form Imidazolidin-2-ones.

Authors:  Hao Li; Feijie Song; Ross A Widenhoefer
Journal:  Adv Synth Catal       Date:  2011-04-18       Impact factor: 5.837

2.  Mechanistic study of gold(I)-catalyzed intermolecular hydroamination of allenes.

Authors:  Z Jane Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

3.  Gold(I)-Catalyzed Intermolecular Hydroamination of Allenes with Arylamines.

Authors:  Alethea N Duncan; Ross A Widenhoefer
Journal:  Synlett       Date:  2010-02       Impact factor: 2.454

4.  Gold(I)-Catalyzed Enantioselective Intramolecular Hydroamination of Allenes with Ureas.

Authors:  Hao Li; Seong Du Lee; Ross A Widenhoefer
Journal:  J Organomet Chem       Date:  2011-01-01       Impact factor: 2.369

5.  Gold(I)-Catalyzed Hydroarylation of Allenes with Indoles.

Authors:  Kristina L Toups; Gordon T Liu; Ross A Widenhoefer
Journal:  J Organomet Chem       Date:  2009-02-15       Impact factor: 2.369

6.  Rhodium phosphine-π-arene intermediates in the hydroamination of alkenes.

Authors:  Zhijian Liu; Hideaki Yamamichi; Sherzod T Madrahimov; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-02-10       Impact factor: 15.419

7.  Formation and utility of azasilacyclopentadienes derived from silacyclopropenes and nitriles.

Authors:  Laura L Anderson; K A Woerpel
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

8.  Gold(I)-catalyzed enantioselective synthesis of pyrazolidines, isoxazolidines, and tetrahydrooxazines.

Authors:  R L Lalonde; Z J Wang; M Mba; A D Lackner; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

9.  Gold-catalyzed intermolecular Markovnikov hydroamination of allenes with secondary amines.

Authors:  Xiaoming Zeng; Michele Soleilhavoup; Guy Bertrand
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

10.  Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.

Authors:  Cong Liu; Ross A Widenhoefer
Journal:  Org Lett       Date:  2007-04-12       Impact factor: 6.005
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.