Literature DB >> 21898736

Regio- and enantioselective hydroamination of dienes by gold(I)/menthol cooperative catalysis.

Osamu Kanno1, Wataru Kuriyama, Z Jane Wang, F Dean Toste.   

Abstract

Alcohol is key: regio- and enantioselective hydroamination of 1,3-dienes has been achieved with the dinuclear catalyst (R)-DTBM-SEGPHOS. The rate and selectivity of the reaction are enhanced by alcohol additives like menthol, which coordinates the cationic gold(I) to generate a Brønsted acid that can participate in catalysis. Mbs=p-methoxybenzenesulfonyl.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID： 21898736      PMCID： PMC3382038          DOI： 10.1002/anie.201104076

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  31 in total

1.  Palladium-catalyzed hydroamination of 1,3-dienes: a colorimetric assay and enantioselective additions.

Authors:  O Löber; M Kawatsura; J F Hartwig
Journal:  J Am Chem Soc       Date:  2001-05-09       Impact factor: 15.419

2.  Chiral Brønsted acid from a cationic gold(I) complex: catalytic enantioselective protonation of silyl enol ethers of ketones.

Authors:  Cheol Hong Cheon; Osamu Kanno; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-08-04       Impact factor: 15.419

Review 3.  Gold and platinum catalysis--a convenient tool for generating molecular complexity.

Authors:  Alois Fürstner
Journal:  Chem Soc Rev       Date:  2009-07-22       Impact factor: 54.564

4.  Gold-catalyzed nucleophilic cyclization of functionalized allenes: a powerful access to carbo- and heterocycles.

Authors:  Norbert Krause; Christian Winter
Journal:  Chem Rev       Date:  2011-02-11       Impact factor: 60.622

5.  Gold(I)-catalyzed intramolecular hydroamination of unactivated alkenes with carboxamides.

Authors:  Christopher F Bender; Ross A Widenhoefer
Journal:  Chem Commun (Camb)       Date:  2006-08-23       Impact factor: 6.222

6.  Catalytic asymmetric hydroamination of non-activated olefins.

Authors:  Kai C Hultzsch
Journal:  Org Biomol Chem       Date:  2005-04-07       Impact factor: 3.876

7.  Gold(I)-catalyzed amination of allylic alcohols with cyclic ureas and related nucleophiles.

Authors:  Paramita Mukherjee; Ross A Widenhoefer
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

8.  A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

9.  Brønsted acid-catalyzed intramolecular hydroamination of protected alkenylamines. Synthesis of pyrrolidines and piperidines.

Authors:  Björn Schlummer; John F Hartwig
Journal:  Org Lett       Date:  2002-05-02       Impact factor: 6.005

10.  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
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  11 in total

1.  Strong electronic and counterion effects on geminal digold formation and reactivity as revealed by gold(I)-aryl model complexes.

Authors:  Dieter Weber; T David Jones; Laura L Adduci; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-25       Impact factor: 15.336

2.  Gold(I)-Mediated Cycloisomerization/Cycloaddition Enables Bioinspired Syntheses of Neonectrolides B-E and Analogues.

Authors:  Thomas J Purgett; Matthew W Dyer; Bryce Bickel; James McNeely; John A Porco
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

3.  Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.

Authors:  Daniel R Wallach; John D Chisholm
Journal:  J Org Chem       Date:  2016-08-10       Impact factor: 4.354

4.  Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes.

Authors:  Xiao-Hui Yang; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-01-27       Impact factor: 15.419

5.  Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst.

Authors:  Nathan J Adamson; Ethan Hull; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2017-05-19       Impact factor: 15.419

6.  Mechanistic Studies of Azaphilic versus Carbophilic Activation by Gold(I) in the Gold/Palladium Dual-Catalyzed Rearrangement of Alkenyl Vinyl Aziridines.

Authors:  Joshua J Hirner; Katrina E Roth; Yili Shi; Suzanne A Blum
Journal:  Organometallics       Date:  2012-10-08       Impact factor: 3.876

7.  Enantioselective thiourea-catalyzed intramolecular cope-type hydroamination.

Authors:  Adam R Brown; Christopher Uyeda; Carolyn A Brotherton; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-04-24       Impact factor: 15.419

8.  Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions.

Authors:  Hengshuai Wang; Shengchao Jiao; Kerong Chen; Xu Zhang; Linxiang Zhao; Dan Liu; Yu Zhou; Hong Liu
Journal:  Beilstein J Org Chem       Date:  2015-03-30       Impact factor: 2.883

9.  Anatomy of gold catalysts: facts and myths.

Authors:  Beatrice Ranieri; Imma Escofet; Antonio M Echavarren
Journal:  Org Biomol Chem       Date:  2015-06-09       Impact factor: 3.876

Review 10.  New developments in gold-catalyzed manipulation of inactivated alkenes.

Authors:  Michel Chiarucci; Marco Bandini
Journal:  Beilstein J Org Chem       Date:  2013-11-21       Impact factor: 2.883
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