Literature DB >> 24920312

Gold-catalyzed diastereoselective cycloisomerization of alkylidene-cyclopropane-bearing 1,6-diynes.

Hongchao Zheng1, Laura L Adduci, Ryan J Felix, Michel R Gagné.   

Abstract

An unprecedented gold-catalyzed diastereoselective cycloisomerization of 1,6-diynes bearing an alkylidene cyclopropane moiety has been developed. This methodology enables rapid access to a variety of 1,2-trimethylenenorbornanes, which are important building blocks in the preparations of abiotic and sesquiterpene core structures.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  1,6-diynes; cycloisomerization; cyclopropylidenes; gold catalysis; synthetic methods

Mesh：

Substances：

Year:  2014        PMID： 24920312      PMCID： PMC4120096          DOI： 10.1002/anie.201405147

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


  41 in total

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Authors:  Norbert Krause; Christian Winter
Journal:  Chem Rev       Date:  2011-02-11       Impact factor: 60.622

6.  Dinuclear gold catalysis: are two gold centers better than one?

Authors:  Adrián Gómez-Suárez; Steven P Nolan
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-18       Impact factor: 15.336

7.  Synthesis of fused carbocycles via a selective 6-endo dig gold(I)-catalyzed carbocyclization.

Authors:  Francis Barabé; Patrick Levesque; Ilia Korobkov; Louis Barriault
Journal:  Org Lett       Date:  2011-09-15       Impact factor: 6.005

8.  A concise total synthesis of pyrovellerolactone using a rhodium-catalyzed [(3 + 2) + 2] carbocyclization reaction.

Authors:  P Andrew Evans; Phillip A Inglesby; Kathryn Kilbride
Journal:  Org Lett       Date:  2013-03-29       Impact factor: 6.005

9.  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

10.  Bromine radical-mediated sequential radical rearrangement and addition reaction of alkylidenecyclopropanes.

Authors:  Takashi Kippo; Kanako Hamaoka; Ilhyong Ryu
Journal:  J Am Chem Soc       Date:  2012-12-28       Impact factor: 15.419
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  4 in total

1.  Gold(i)-catalyzed addition of aldehydes to cyclopropylidene bearing 6-aryl-1,5-enynes.

Authors:  Christina A Roselli; Michel R Gagné
Journal:  Org Biomol Chem       Date:  2016-11-29       Impact factor: 3.876

2.  Synthesis of Five-Porphyrin Nanorings by Using Ferrocene and Corannulene Templates.

Authors:  Pengpeng Liu; Yutaka Hisamune; Martin D Peeks; Barbara Odell; Juliane Q Gong; Laura M Herz; Harry L Anderson
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-23       Impact factor: 15.336

3.  Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes.

Authors:  De-Yao Li; Yin Wei; Ilan Marek; Xiang-Ying Tang; Min Shi
Journal:  Chem Sci       Date:  2015-06-24       Impact factor: 9.825

4.  Gold(I)-Catalyzed Cycloisomerization of 3-Alkoxyl-1,6-diynes: A Facile Access to Bicyclo[2.2.1]hept-5-en-2-ones.

Authors:  Chao Hu; Tao Wang; Matthias Rudolph; Thomas Oeser; Abdullah M Asiri; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336
  4 in total

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