Literature DB >> 30117646

Synthesis of Spirocyclic Ethers by Enantioselective Copper-Catalyzed Carboetherification of Alkenols.

Shuklendu D Karyakarte1, Chanchamnan Um1, Ilyas A Berhane1, Sherry R Chemler1.   

Abstract

Spirocyclic ethers can be found in bioactive compounds. This copper-catalyzed enantioselective alkene carboetherification provides 5,5-, 5,6- and 6,6-spirocyclic products containing fully substituted chiral carbon centers with up to 99 % enantiomeric excess. This reaction features the formation of two rings from acyclic substrates, 1,1-disubstituted alkenols functionalized with either arenes, alkenes, or alkynes, and clearly constitutes a powerful way to synthesize chiral spirocyclic ethers.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; cyclizations; enantioselectivity; spiro-compounds; synthetic methods

Mesh：

Substances：

Year:  2018        PMID： 30117646      PMCID： PMC6375082          DOI： 10.1002/anie.201808554

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


  28 in total

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Journal:  Chembiochem       Date:  2011-05-06       Impact factor: 3.164

4.  Organocatalytic asymmetric direct C(sp3)-H functionalization of ethers: a highly efficient approach to chiral spiroethers.

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Journal:  Angew Chem Int Ed Engl       Date:  2012-07-31       Impact factor: 15.336

Review 5.  The use of spirocyclic scaffolds in drug discovery.

Authors:  Yajun Zheng; Colin M Tice; Suresh B Singh
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6.  Palladium-Catalyzed Cascade Assembly of Tricyclic Spiroethers from Diene-Alcohol Precursors.

Authors:  David Lankri; Yelena Mostinski; Dmitry Tsvelikhovsky
Journal:  J Org Chem       Date:  2017-08-25       Impact factor: 4.354

7.  Synthetic Study of Phainanoids. Highly Diastereoselective Construction of the 4,5-Spirocycle via Palladium-Catalyzed Intramolecular Alkenylation.

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8.  Diastereoselective Synthesis of CF3- and CF2H-Substituted Spiroethers from Aryl-Fused Cycloalkenylalkanols by Photoredox Catalysis.

Authors:  Naoki Noto; Takashi Koike; Munetaka Akita
Journal:  J Org Chem       Date:  2016-06-29       Impact factor: 4.354

9.  Enantioselective functionalization of radical intermediates in redox catalysis: copper-catalyzed asymmetric oxytrifluoromethylation of alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
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10.  Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-06-23       Impact factor: 15.419
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  6 in total

1.  Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers.

Authors:  Dake Chen; Ilyas A Berhane; Sherry R Chemler
Journal:  Org Lett       Date:  2020-06-04       Impact factor: 6.005

2.  Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers.

Authors:  Ilyas A Berhane; Ameya S Burde; Jonathan J Kennedy-Ellis; Eva Zurek; Sherry R Chemler
Journal:  Chem Commun (Camb)       Date:  2021-09-30       Impact factor: 6.065

3.  Enantioselective, Aerobic Copper-Catalyzed Intramolecular Carboamination and Carboetherification of Unactivated Alkenes.

Authors:  Tomasz Wdowik; Samuel L Galster; Raul L L Carmo; Sherry R Chemler
Journal:  ACS Catal       Date:  2020-07-16       Impact factor: 13.084

4.  Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols.

Authors:  Dake Chen; Sherry R Chemler
Journal:  Org Lett       Date:  2018-10-11       Impact factor: 6.005

5.  Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.

Authors:  Ameya S Burde; Shuklendu D Karyakarte; Eric D Sylvester; Sherry R Chemler
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6.  Asymmetric radical carboesterification of dienes.

Authors:  Xiaotao Zhu; Wujun Jian; Meirong Huang; Daliang Li; Yajun Li; Xinhao Zhang; Hongli Bao
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  6 in total

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