Literature DB >> 22145621

Enantioselective bromocycloetherification by Lewis base/chiral Brønsted acid cooperative catalysis.

Scott E Denmark1, Matthew T Burk.   

Abstract

A binary catalyst system for the enantioselective bromocycloetherification of 5-arylpentenols is described. The combination of an achiral Lewis base and a chiral Brønsted acid affords good enantioselectivities for the cyclization of Z configured 5-arylpentenols to form bromomethyltetrahydrofurans. The constitutional site selectivity is highly dependent upon the aromatic substituent and the configuration of the double bond.
© 2011 American Chemical Society

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Year:  2011        PMID： 22145621      PMCID： PMC3238797          DOI： 10.1021/ol203033k

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


  14 in total

1.  Lewis base catalysis of bromo- and iodolactonization, and cycloetherification.

Authors:  Scott E Denmark; Matthew T Burk
Journal:  Proc Natl Acad Sci U S A       Date:  2010-08-12       Impact factor: 11.205

2.  Asymmetric bromolactonization catalyzed by a C3-symmetric chiral trisimidazoline.

Authors:  Kenichi Murai; Tomoyo Matsushita; Akira Nakamura; Shunsuke Fukushima; Masato Shimura; Hiromichi Fujioka
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-22       Impact factor: 15.336

Review 3.  Marine natural products.

Authors:  John W Blunt; Brent R Copp; Murray H G Munro; Peter T Northcote; Michèle R Prinsep
Journal:  Nat Prod Rep       Date:  2010-12-13       Impact factor: 13.423

Review 4.  Small-molecule H-bond donors in asymmetric catalysis.

Authors:  Abigail G Doyle; Eric N Jacobsen
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

5.  Enantioselective bromoaminocyclization using amino-thiocarbamate catalysts.

Authors:  Ling Zhou; Jie Chen; Chong Kiat Tan; Ying-Yeung Yeung
Journal:  J Am Chem Soc       Date:  2011-05-03       Impact factor: 15.419

6.  Preparative and mechanistic studies toward the rational development of catalytic, enantioselective selenoetherification reactions.

Authors:  Scott E Denmark; Dipannita Kalyani; William R Collins
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

7.  Enantioselective haloetherification by asymmetric opening of meso-halonium ions.

Authors:  Ulrich Hennecke; Christian H Müller; Roland Fröhlich
Journal:  Org Lett       Date:  2011-02-08       Impact factor: 6.005

8.  Aminothiocarbamate-catalyzed asymmetric bromolactonization of 1,2-disubstituted olefinic acids.

Authors:  Chong Kiat Tan; Ling Zhou; Ying-Yeung Yeung
Journal:  Org Lett       Date:  2011-04-26       Impact factor: 6.005

9.  Chiral Brønsted acid catalyzed enantioselective Mannich-type reaction.

Authors:  Masahiro Yamanaka; Junji Itoh; Kohei Fuchibe; Takahiko Akiyama
Journal:  J Am Chem Soc       Date:  2007-05-04       Impact factor: 15.419

10.  On the absolute configurational stability of bromonium and chloronium ions.

Authors:  Scott E Denmark; Matthew T Burk; Andrew J Hoover
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419
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  22 in total

1.  Bifunctional catalyst promotes highly enantioselective bromolactonizations to generate stereogenic C-Br bonds.

Authors:  Daniel H Paull; Chao Fang; James R Donald; Andrew D Pansick; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2012-06-27       Impact factor: 15.419

2.  Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

Authors:  Yan Miller; Lei Miao; Azade S Hosseini; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2012-07-05       Impact factor: 15.419

3.  Regio- and Enantioselective Bromocyclization of Difluoroalkenes as a Strategy to Access Tetrasubstituted Difluoromethylene-Containing Stereocenters.

Authors:  Edward Miller; Suhong Kim; Katarina Gibson; Jeffrey S Derrick; F Dean Toste
Journal:  J Am Chem Soc       Date:  2020-04-30       Impact factor: 15.419

4.  Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.

Authors:  Michael T Bovino; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-05       Impact factor: 15.336

5.  5-(Methylthio)tetrazoles as Versatile Synthons in the Stereoselective Synthesis of Polycyclic Pyrazolines via Photoinduced Intramolecular Nitrile Imine-Alkene 1,3-Dipolar Cycloaddition.

Authors:  Daniel Pla; Derek S Tan; David Y Gin
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

6.  Development and mechanism of an enantioselective bromocycloetherification reaction via Lewis base/chiral Brønsted acid cooperative catalysis.

Authors:  Scott E Denmark; Matthew T Burk
Journal:  Chirality       Date:  2013-11-07       Impact factor: 2.437

Review 7.  Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

Authors:  Scott E Denmark; William E Kuester; Matthew T Burk
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

8.  Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed iodolactonization.

Authors:  Mark C Dobish; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

9.  Investigating the Enantiodetermining Step of a Chiral Lewis Base Catalyzed Bromocycloetherification of Privileged Alkenes.

Authors:  Dietrich Böse; Scott E Denmark
Journal:  Synlett       Date:  2017-11-13       Impact factor: 2.454

10.  Iron-Catalyzed Diastereoselective Intramolecular Olefin Aminobromination with Bromide Ion.

Authors:  Jun-Shan Tian; Cheng-Liang Zhu; Yun-Rong Chen; Hao Xu
Journal:  Synthesis (Stuttg)       Date:  2015-06       Impact factor: 3.157
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