Literature DB >> 21932856

Asymmeric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates.

Xiaochen Wang1, Xinfang Xu, Peter Y Zavalij, Michael P Doyle.   

Abstract

With metal carbene access to dipolar intermediates, 3,6-dihydro-1,2-oxazines are produced in high yields by dirhodium(II) carboxylate catalyzed reactions between nitrones and a β-TBSO-substituted vinyldiazoacetate. High enantiocontrol occurs with catalysis by N-phthaloyl-(S)-(amino acid)-ligated dirhodium carboxylates for [3 + 3]-cycloaddition reactions with both acyclic and cyclic nitrones.

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Year:  2011        PMID： 21932856      PMCID： PMC3192303          DOI： 10.1021/ja207664r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  30 in total

1.  A highly selective, organocatalytic route to chiral dihydro-1,2-oxazines.

Authors:  Sirirat Kumarn; David M Shaw; Deborah A Longbottom; Steven V Ley
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

2.  Iron and ruthenium Lewis acid catalyzed asymmetric 1,3-dipolar cycloaddition reactions between nitrones and enals.

Authors:  Florian Viton; Gérald Bernardinelli; E Peter Kündig
Journal:  J Am Chem Soc       Date:  2002-05-08       Impact factor: 15.419

3.  Rhodium-catalyzed [3 + 2] annulation of indoles.

Authors:  Yajing Lian; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

4.  Solvent enhancement of reaction selectivity: a unique property of cationic chiral dirhodium carboxamidates.

Authors:  Xiaochen Wang; Carolin Weigl; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2011-05-27       Impact factor: 15.419

5.  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

6.  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

7.  Gold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters.

Authors:  Nathan D Shapiro; Yun Shi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

8.  Sugars, alkaloids, and heteroaromatics: exploring heterocyclic chemistry with alkoxyallenes.

Authors:  Malte Brasholz; Hans-Ulrich Reissig; Reinhold Zimmer
Journal:  Acc Chem Res       Date:  2009-01-20       Impact factor: 22.384

9.  Iron- and ruthenium-Lewis acid catalyzed asymmetric 1,3-dipolar cycloaddition reactions between enals and diaryl nitrones.

Authors:  Andrei Bădoiu; Gerald Bernardinelli; Jiri Mareda; E Peter Kündig; Florian Viton
Journal:  Chem Asian J       Date:  2008-09-01

10.  Chiral DBFOX/Ph complex catalyzed enantioselective nitrone cycloadditions to alpha,beta-unsaturated aldehydes.

Authors:  Moto Shirahase; Shuji Kanemasa; Yoji Oderaotoshi
Journal:  Org Lett       Date:  2004-03-04       Impact factor: 6.005
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  26 in total

1.  Gold(I)-catalyzed enantioselective [3+2] and [3+3] cycloaddition reactions of propargyl acetals/ketals.

Authors:  Cristina Navarro; Nathan D Shapiro; Maurizio Bernasconi; Takahiro Horibe; F Dean Toste
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

2.  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

3.  Unexpected catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides that form 5-arylaminofuran-2(3H)-one-4-carboxylates.

Authors:  Xinfang Xu; Dmitry Shabashov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2012-01-24       Impact factor: 6.005

4.  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

5.  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 6.  Catalytic asymmetric cycloaddition reactions of enoldiazo compounds.

Authors:  Kostiantyn O Marichev; Michael P Doyle
Journal:  Org Biomol Chem       Date:  2019-04-24       Impact factor: 3.876

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

Authors:  Damien Valette; Yajing Lian; John P Haydek; Kenneth I Hardcastle; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-16       Impact factor: 15.336

Review 8.  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

9.  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

10.  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
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