Literature DB >> 21302896

Enantioselective haloetherification by asymmetric opening of meso-halonium ions.

Ulrich Hennecke1, Christian H Müller, Roland Fröhlich.   

Abstract

A new approach to enantioselective haloetherification reactions via desymmetrization of in situ-generated meso-halonium ions is described. The combination of N-haloamides as a halogen source and sodium salts of chiral phosphoric acids as catalysts can be used for the cyclization of symmetrical ene-diol substrates, yielding the haloetherification products under practical conditions in enantioenriched form.

Entities:  

Year:  2011        PMID： 21302896     DOI： 10.1021/ol1028805

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


  17 in total

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

Authors:  Scott E Denmark; Matthew T Burk
Journal:  Org Lett       Date:  2011-12-06       Impact factor: 6.005

2.  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

3.  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

4.  The progression of chiral anions from concepts to applications in asymmetric catalysis.

Authors:  Robert J Phipps; Gregory L Hamilton; F Dean Toste
Journal:  Nat Chem       Date:  2012-07-24       Impact factor: 24.427

5.  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

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.  Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides.

Authors:  Bardia Soltanzadeh; Arvind Jaganathan; Richard J Staples; Babak Borhan
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-25       Impact factor: 15.336

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.  Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications.

Authors:  Daniel W Klosowski; J Caleb Hethcox; Daniel H Paull; Chao Fang; James R Donald; Christopher R Shugrue; Andrew D Pansick; Stephen F Martin
Journal:  J Org Chem       Date:  2018-05-22       Impact factor: 4.354
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