Literature DB >> 30336677

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

Dake Chen1, Sherry R Chemler1.   

Abstract

Enantiomerically enriched phthalans were synthesized efficiently via an enantioselective copper-catalyzed alkene carboetherification reaction. In this reaction, 2-vinylbenzyl alcohols enantioselectively cyclize then couple with vinylarenes. The utility of the method was demonstrated by the enantioselective synthesis of ( R)-fluspidine, a σ1 receptor ligand.

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Year:  2018        PMID： 30336677      PMCID： PMC6459690          DOI： 10.1021/acs.orglett.8b02766

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


  22 in total

1.  Synthesis, characterization, and metabolism studies of fluspidine enantiomers.

Authors:  Katharina Holl; Evamaria Falck; Jens Köhler; Dirk Schepmann; Hans-Ulrich Humpf; Peter Brust; Bernhard Wünsch
Journal:  ChemMedChem       Date:  2013-10-15       Impact factor: 3.466

2.  Pd-catalyzed intramolecular oxyalkynylation of alkenes with hypervalent iodine.

Authors:  Stefano Nicolai; Stéphane Erard; Davinia Fernández González; Jérôme Waser
Journal:  Org Lett       Date:  2010-01-15       Impact factor: 6.005

3.  Catalytic and asymmetric fluorolactonisations of carboxylic acids through anion phase transfer.

Authors:  Dixit Parmar; Modhu Sudan Maji; Magnus Rueping
Journal:  Chemistry       Date:  2013-12-04       Impact factor: 5.236

4.  Synthesis, pharmacological activity and structure affinity relationships of spirocyclic σ(1) receptor ligands with a (2-fluoroethyl) residue in 3-position.

Authors:  Eva Grosse Maestrup; Christian Wiese; Dirk Schepmann; Peter Brust; Bernhard Wünsch
Journal:  Bioorg Med Chem       Date:  2010-11-11       Impact factor: 3.641

5.  Enantioselective copper-catalyzed carboetherification of unactivated alkenes.

Authors:  Michael T Bovino; Timothy W Liwosz; Nicole E Kendel; Yan Miller; Nina Tyminska; Eva Zurek; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-05       Impact factor: 15.336

Review 6.  Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Authors:  Richard I McDonald; Guosheng Liu; Shannon S Stahl
Journal:  Chem Rev       Date:  2011-03-23       Impact factor: 60.622

7.  CN-assisted oxidative cyclization of cyano cinnamates and styrene derivatives: a facile entry to 3-substituted chiral phthalides.

Authors:  R Santhosh Reddy; I N Chaithanya Kiran; Arumugam Sudalai
Journal:  Org Biomol Chem       Date:  2012-04-03       Impact factor: 3.876

8.  An enantioselective approach toward 3,4-dihydroisocoumarin through the bromocyclization of styrene-type carboxylic acids.

Authors:  Jie Chen; Ling Zhou; Chong Kiat Tan; Ying-Yeung Yeung
Journal:  J Org Chem       Date:  2011-12-29       Impact factor: 4.354

9.  Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes.

Authors:  Guozhu Zhang; Li Cui; Yanzhao Wang; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-02-10       Impact factor: 15.419

10.  Phthalides by rhodium-catalyzed ketone hydroacylation.

Authors:  Diem H T Phan; Byoungmoo Kim; Vy M Dong
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419
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  4 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.  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
Journal:  Chem Commun (Camb)       Date:  2021-01-05       Impact factor: 6.222

4.  Asymmetric radical carboesterification of dienes.

Authors:  Xiaotao Zhu; Wujun Jian; Meirong Huang; Daliang Li; Yajun Li; Xinhao Zhang; Hongli Bao
Journal:  Nat Commun       Date:  2021-11-18       Impact factor: 14.919
  4 in total

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