Literature DB >> 17428061

Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.

Cong Liu1, Ross A Widenhoefer.   

Abstract

Treatment of 2-allenyl indole 4 with a catalytic 1:2 mixture of [(S)-2]Au2Cl2 [(S)-2 = (S)-3,5-tBu-4-MeO-MeOBIPHEP] and AgBF4 in toluene at -10 degrees C for 17 h led to isolation of tetrahydrocarbazole 5 in 88% yield with 92% ee. The protocol was effective for the cyclization of terminally disubstituted allenes and for the formation of seven-membered rings.

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Year:  2007        PMID： 17428061      PMCID： PMC2747371          DOI： 10.1021/ol070483c

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  31 in total

1.  A New Gold-Catalyzed C-C Bond Formation This work was supported by the Deutsche Forschungsgemeinschaft (Ha 1932/5-1, Ha 1932/6-1) and the Fonds der Chemischen Industrie. Gold salts were donated by Degussa-Hüls AG. A.S.K.H. is indebted to Prof. M. Göbel for laboratory space.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-07-03       Impact factor: 15.336

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Authors:  Michael A Tarselli; Ann Liu; Michel R Gagné
Journal:  Tetrahedron       Date:  2009-02       Impact factor: 2.457

3.  Highly active Au(I) catalyst for the intramolecular exo-hydrofunctionalization of allenes with carbon, nitrogen, and oxygen nucleophiles.

Authors:  Zhibin Zhang; Cong Liu; Robert E Kinder; Xiaoqing Han; Hua Qian; Ross A Widenhoefer
Journal:  J Am Chem Soc       Date:  2006-07-19       Impact factor: 15.419

4.  Intramolecular hydroarylation of alkynes catalyzed by platinum or gold: mechanism and endo selectivity.

Authors:  Cristina Nevado; Antonio M Echavarren
Journal:  Chemistry       Date:  2005-05-06       Impact factor: 5.236

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7.  Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway.

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Journal:  J Am Chem Soc       Date:  2008-03-22       Impact factor: 15.419

8.  Gold(I)-catalyzed intramolecular hydroarylation of allenes.

Authors:  Michael A Tarselli; Michel R Gagné
Journal:  J Org Chem       Date:  2008-02-16       Impact factor: 4.354

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  25 in total

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Journal:  Chem Sci       Date:  2011-06-24       Impact factor: 9.825

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Authors:  Charles A Mullen; Alison N Campbell; Michel R Gagné
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3.  Asymmetric gold-catalyzed lactonizations in water at room temperature.

Authors:  Sachin Handa; Daniel J Lippincott; Donald H Aue; Bruce H Lipshutz
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-14       Impact factor: 15.336

4.  Mechanistic study of gold(I)-catalyzed intermolecular hydroamination of allenes.

Authors:  Z Jane Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

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

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Journal:  J Am Chem Soc       Date:  2011-03-23       Impact factor: 15.419

6.  Development and initial application of a hybridization-independent, DNA-encoded reaction discovery system compatible with organic solvents.

Authors:  Mary M Rozenman; Matthew W Kanan; David R Liu
Journal:  J Am Chem Soc       Date:  2007-11-10       Impact factor: 15.419

7.  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

8.  One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles.

Authors:  Qiong-Jie Liu; Wen-Guang Yan; Lijia Wang; X Peter Zhang; Yong Tang
Journal:  Org Lett       Date:  2015-08-07       Impact factor: 6.005

9.  Gold(I)-catalyzed intramolecular hydroarylation of allenes.

Authors:  Michael A Tarselli; Michel R Gagné
Journal:  J Org Chem       Date:  2008-02-16       Impact factor: 4.354

10.  Gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols.

Authors:  Florian Kleinbeck; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-07-08       Impact factor: 15.419
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