Literature DB >> 20518531

Gold(I)-catalyzed enantioselective polycyclization reactions.

Steven G Sethofer1, Timo Mayer, F Dean Toste.   

Abstract

A series of enantioselective polycyclization reactions, catalyzed by a cationic bisphosphine gold complexes, are described. The polycyclization reactions, which employ an alkyne as an initiating group, begin with a gold-promoted 6-exo-dig cyclization and can be terminated with a variety of nucleophiles including carboxylic acids, phenols, sulfonamides, and electron-rich aryl groups. This method allows for the preparation of up to four bonds in a single operation with excellent diastereo- and enantioselectivity.

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Year:  2010        PMID: 20518531      PMCID: PMC2888676          DOI: 10.1021/ja103544p

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


  31 in total

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Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-08-18       Impact factor: 15.336

2.  The mechanistic puzzle of transition-metal-catalyzed skeletal rearrangements of enynes.

Authors:  Cristina Nieto-Oberhuber; Salomé López; Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal:  Chemistry       Date:  2006-08-07       Impact factor: 5.236

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Authors:  Ryan A Yoder; Jeffrey N Johnston
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

4.  Gold(I)-catalyzed [2 + 2]-cycloaddition of allenenes.

Authors:  Michael R Luzung; Pablo Mauleón; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-09-21       Impact factor: 15.419

5.  Asymmetric oxidative cation/olefin cyclization of polyenes: evidence for reversible cascade cyclization.

Authors:  Charles A Mullen; Alison N Campbell; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 6.  Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective.

Authors:  Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal:  Chem Rev       Date:  2008-07-18       Impact factor: 60.622

7.  On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions.

Authors:  Alois Fürstner; Louis Morency
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  Gold-catalyzed assembly of heterobicyclic systems.

Authors:  Liming Zhang; Sergey A Kozmin
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

9.  Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites.

Authors:  Akira Sakakura; Atsushi Ukai; Kazuaki Ishihara
Journal:  Nature       Date:  2007-02-22       Impact factor: 49.962

10.  Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

Authors:  Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

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  38 in total

1.  Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes.

Authors:  Patrick T Bohan; F Dean Toste
Journal:  J Am Chem Soc       Date:  2017-08-03       Impact factor: 15.419

2.  Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Chem Sci       Date:  2013-07-01       Impact factor: 9.825

3.  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

4.  Terminating platinum-initiated cation-olefin reactions with simple alkenes.

Authors:  Joseph G Sokol; Chandra Sekhar Korapala; Peter S White; Jennifer J Becker; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-13       Impact factor: 15.336

5.  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

6.  Enantioselective cyclizations of silyloxyenynes catalyzed by cationic metal phosphine complexes.

Authors:  Jean-François Brazeau; Suyan Zhang; Ignacio Colomer; Britton K Corkey; F Dean Toste
Journal:  J Am Chem Soc       Date:  2012-01-31       Impact factor: 15.419

7.  Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Authors:  Weiwei Zi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

8.  Enantioselective synthesis of angularly substituted 1-azabicylic rings: coupled dynamic kinetic epimerization and chirality transfer.

Authors:  Zachary D Aron; Tatsuya Ito; Tricia L May; Larry E Overman; Jocelyn Wang
Journal:  J Org Chem       Date:  2013-09-10       Impact factor: 4.354

9.  A Cyclization/Oxygenation Scheme for the Conversion of Polyenes into C3-Oxygenated Polycycles.

Authors:  Michael J Geier; Michel R Gagné
Journal:  Organometallics       Date:  2013-01-07       Impact factor: 3.876

10.  Catalytic enantioselective cyclization and C3-fluorination of polyenes.

Authors:  Nikki A Cochrane; Ha Nguyen; Michel R Gagne
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

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