Literature DB >> 26031403

Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement.

Hongmiao Wu1,2, Weiwei Zi1, Guigen Li2, Hongjian Lu3, F Dean Toste4.   

Abstract

An enantioselective alkoxylation/Claisen rearrangement reaction was achieved by a strategic desymmetrization of 1,4-dienes under the catalysis of (S)-DTBM-Segphos(AuCl)2/AgBF4. This reaction system was highly selective for the formation of 3,3-rearrangement products, providing cycloheptenes with various substitutions in good yield and good to excellent enantioselectivity. This transformation was further extended to bicyclic ring substrates, providing the opportunity to easily assemble 5,6- and 6,7-fused ring systems.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Claisen rearrangement; alkoxylation; desymmetrization; enantioselectivity; gold

Mesh：

Substances：

Year:  2015        PMID： 26031403      PMCID： PMC4529066          DOI： 10.1002/anie.201503357

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


  50 in total

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3.  Gold catalysis: enantiotopos selection.

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4.  Catalytic asymmetric Claisen rearrangement of unactivated allyl vinyl ethers.

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Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

5.  Palladium-catalyzed intramolecular asymmetric C-H functionalization/cyclization reaction of metallocenes: an efficient approach toward the synthesis of planar chiral metallocene compounds.

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Journal:  J Am Chem Soc       Date:  2014-03-13       Impact factor: 15.419

6.  The tandem intermolecular hydroalkoxylation/Claisen rearrangement.

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Journal:  Angew Chem Int Ed Engl       Date:  2014-07-14       Impact factor: 15.336

8.  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

9.  Catalytic enantioselective claisen rearrangements of O-allyl β-ketoesters.

Authors:  Christopher Uyeda; Andreas R Rötheli; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-10       Impact factor: 15.336

10.  Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst.

Authors:  Christopher Uyeda; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2008-06-25       Impact factor: 15.419
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3.  Gold(I)-Catalyzed Cycloisomerization of 3-Alkoxyl-1,6-diynes: A Facile Access to Bicyclo[2.2.1]hept-5-en-2-ones.

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Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336
  3 in total

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