Literature DB >> 22807172

Alkynoate synthesis through the vinylogous reactivity of rhodium(II) carbenoids.

Damien Valette1, Yajing Lian, John P Haydek, Kenneth I Hardcastle, Huw M L Davies.   

Abstract

Siloxy group migration: A rhodium(II) carbenoid approach has been developed for the synthesis of alkynoates. This transformation combines the addition of enol ethers at the vinylogous position of β-siloxy-substituted vinyldiazo derivatives with a siloxy group migration to give the products as single diastereomers.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22807172      PMCID： PMC3580044          DOI： 10.1002/anie.201204047

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


  21 in total

1.  Catalytic asymmetric C-H activation of silyl enol ethers as an equivalent of an asymmetric Michael reaction.

Authors:  H M Davies; P Ren
Journal:  J Am Chem Soc       Date:  2001-03-07       Impact factor: 15.419

2.  Intramolecular reductive ketone-alkynoate coupling reaction promoted by (η2-propene)titanium.

Authors:  Christian Schäfer; Michel Miesch; Laurence Miesch
Journal:  Org Biomol Chem       Date:  2012-03-12       Impact factor: 3.876

3.  Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion.

Authors:  Huw M L Davies; Rohan E J Beckwith
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

4.  On the mechanism and selectivity of the combined C-H activation/Cope rearrangement.

Authors:  Jørn H Hansen; Timothy M Gregg; Stephanie R Ovalles; Yajing Lian; Jochen Autschbach; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2011-03-08       Impact factor: 15.419

5.  Palladium-catalyzed intramolecular hydroarylation of 4-benzofuranyl alkynoates. Approach to angelicin derivatives.

Authors:  Tsugio Kitamura; Kensuke Otsubo
Journal:  J Org Chem       Date:  2012-02-28       Impact factor: 4.354

6.  Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.

Authors:  Xinfang Xu; Maxim O Ratnikov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2011-10-27       Impact factor: 6.005

7.  Asymmetric Synthesis of 2,3-Dihydrofurans by Reaction of Rhodium-Stabilized Vinylcarbenoids with Vinyl Ethers.

Authors:  Huw M. L. Davies; Gulzar Ahmed; Rebecca L. Calvo; Melvyn Rowen Churchill; David G. Churchill
Journal:  J Org Chem       Date:  1998-04-17       Impact factor: 4.354

8.  Rhodium carbenoid approach for introduction of 4-substituted (Z)-pent-2-enoates into sterically encumbered pyrroles and indoles.

Authors:  Yajing Lian; Huw M L Davies
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

9.  Asymmetric [4 + 3] cycloadditions between vinylcarbenoids and dienes: application to the total synthesis of the natural product (-)-5-epi-vibsanin E.

Authors:  Brett D Schwartz; Justin R Denton; Yajing Lian; Huw M L Davies; Craig M Williams
Journal:  J Am Chem Soc       Date:  2009-06-17       Impact factor: 15.419

10.  Selectivity enhancement in the Rh(II)-catalyzed cyclopropanation of styrene with (silanyloxyvinyl)diazoacetates.

Authors:  Paul Müller; Gérald Bernardinelli; Yves F Allenbach; Maria Ferri; Howard D Flack
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005
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  10 in total

1.  Rh2(R-TPCP)4-catalyzed enantioselective [3+2]-cycloaddition between nitrones and vinyldiazoacetates.

Authors:  Changming Qin; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2013-09-20       Impact factor: 15.419

2.  Highly enantioselective dearomatizing formal [3+3] cycloaddition reactions of N-acyliminopyridinium ylides with electrophilic enol carbene intermediates.

Authors:  Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

3.  Reversal of the regiochemistry in the rhodium-catalyzed [4+3] cycloaddition between vinyldiazoacetates and dienes.

Authors:  Pablo E Guzmán; Yajing Lian; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-29       Impact factor: 15.336

Review 4.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

5.  Rhodium-catalyzed enantioselective vinylogous addition of enol ethers to vinyldiazoacetates.

Authors:  Austin G Smith; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2012-10-29       Impact factor: 15.419

6.  Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene.

Authors:  Paul A Allegretti; Khoi Huynh; Tarik J Ozumerzifon; Eric M Ferreira
Journal:  Org Lett       Date:  2015-12-14       Impact factor: 6.005

7.  Dirhodium(II)-catalyzed formal [3+2+1]-annulation of azomethine imines with two molecules of a diazo ketone.

Authors:  Xinfang Xu; Xichen Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2013-04-07       Impact factor: 6.222

8.  Vinylogous reactivity of enol diazoacetates with donor-acceptor substituted hydrazones. Synthesis of substituted pyrazole derivatives.

Authors:  Xinfang Xu; Peter Y Zavalij; Wenhao Hu; Michael P Doyle
Journal:  J Org Chem       Date:  2013-01-24       Impact factor: 4.354

9.  Silver-catalyzed vinylogous fluorination of vinyl diazoacetates.

Authors:  Changming Qin; Huw M L Davies
Journal:  Org Lett       Date:  2013-11-14       Impact factor: 6.005

10.  Finding Opportunities from Surprises and Failures. Development of Rhodium-Stabilized Donor/Acceptor Carbenes and Their Application to Catalyst-Controlled C-H Functionalization.

Authors:  Huw M L Davies
Journal:  J Org Chem       Date:  2019-10-10       Impact factor: 4.354
  10 in total

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