Literature DB >> 19236093

Gold(I)-catalyzed enantioselective synthesis of benzopyrans via rearrangement of allylic oxonium intermediates.

Minoru Uemura1, Iain D G Watson, Mikimoto Katsukawa, F Dean Toste.   

Abstract

The first transition metal catalyzed asymmetric carboalkoxylation reaction of propargyl esters is described. The (R)-MeO-DTBM-BIPHEP(AuCl)(2)-catalyzed reactions allow for the construction of benzopyrans containing quaternary stereocenters with excellent enantioselectivity. Experimental evidence supports a mechanism proceeding via the generation of a stabilized carbocation from an allylic oxonium intermediate and subsequent trapping by a chiral allylgold(I) spieces.

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Year:  2009        PMID： 19236093      PMCID： PMC2664525          DOI： 10.1021/ja900155x

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


  21 in total

1.  Molecular diversity through gold catalysis with alkynes.

Authors:  Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal:  Chem Commun (Camb)       Date:  2006-11-09       Impact factor: 6.222

Review 2.  Relativistic effects in homogeneous gold catalysis.

Authors:  David J Gorin; F Dean Toste
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

3.  Golden carousel in catalysis: the cationic gold/propargylic ester cycle.

Authors:  Andrea Correa; Nicolas Marion; Louis Fensterbank; Max Malacria; Steven P Nolan; Luigi Cavallo
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Gold-catalyzed organic reactions.

Authors:  A Stephen K Hashmi
Journal:  Chem Rev       Date:  2007-06-20       Impact factor: 60.622

5.  Gold(I)-catalyzed cycloisomerization of 3-methoxy-1,6-enynes featuring tandem cyclization and [3,3]-sigmatropic rearrangement.

Authors:  Hyo J Bae; Baburaj Baskar; Sang E An; Jae Y Cheong; Daniel T Thangadurai; In-Chul Hwang; Young H Rhee
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Gold(I)-catalyzed stereoselective olefin cyclopropanation.

Authors:  Magnus J Johansson; David J Gorin; Steven T Staben; F Dean Toste
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

7.  Synthesis of indenyl ethers by gold(I)-catalyzed intramolecular carboalkoxylation of alkynes.

Authors:  Pascal Dubé; F Dean Toste
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

8.  Synthesis of 2,3-disubstituted benzofurans by platinum-olefin-catalyzed carboalkoxylation of o-alkynylphenyl acetals.

Authors:  Itaru Nakamura; Yuya Mizushima; Yoshinori Yamamoto
Journal:  J Am Chem Soc       Date:  2005-11-02       Impact factor: 15.419

9.  Ruthenium-catalyzed cyclopropanation of alkenes using propargylic carboxylates as precursors of vinylcarbenoids.

Authors:  Koji Miki; Kouichi Ohe; Sakae Uemura
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354

10.  Fluorenes and styrenes by Au(I)-catalyzed annulation of enynes and alkynes.

Authors:  David J Gorin; Iain D G Watson; F Dean Toste
Journal:  J Am Chem Soc       Date:  2008-03-06       Impact factor: 15.419
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  22 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.  Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement.

Authors:  Hongmiao Wu; Weiwei Zi; Guigen Li; Hongjian Lu; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-01       Impact factor: 15.336

3.  Gold(I)-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition and Mannich reactions of azlactones.

Authors:  Asa D Melhado; Giovanni W Amarante; Z Jane Wang; Marco Luparia; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

4.  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

5.  Phosphoramidite gold(I)-catalyzed diastereo- and enantioselective synthesis of 3,4-substituted pyrrolidines.

Authors:  Ana Z González; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-03-23       Impact factor: 15.419

6.  Chiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters.

Authors:  Yi-Ming Wang; Christian N Kuzniewski; Vivek Rauniyar; Christina Hoong; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-07-28       Impact factor: 15.419

7.  Enantioselective synthesis of cyclic carbamimidates via a three-component reaction of imines, terminal alkynes, and p-toluenesulfonylisocyanate using a monophosphine gold(I) catalyst().

Authors:  Matthew J Campbell; F Dean Toste
Journal:  Chem Sci       Date:  2011-05-12       Impact factor: 9.825

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(I)-catalyzed enantioselective [4 + 2]-cycloaddition of allene-dienes.

Authors:  Ana Z González; F Dean Toste
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

Review 10.  Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.

Authors:  Roohollah Kazem Shiroodi; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2013-06-21       Impact factor: 54.564
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