Literature DB >> 29904236

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

Dietrich Böse1, Scott E Denmark1.   

Abstract

The development of catalytic, enantioselective halofunctionalizations of unactivated alkenes has made significant progress in recent years. However, the identification of generally applicable catalysts for wide range of substrates has yet to be realized. A detailed understanding of the reaction mechanism is essential to guide the formulation of a truly general catalyst. Herein, we present our investigations on the enantiodetermining step of a Lewis base catalyzed bromocycloetherification that provides important insights and design criteria.

Entities:  

Keywords:  Lewis base; alkenes; bromiranium ions; bromocycloetherification; halofunctionalization; selenophosphoramides

Year:  2017        PMID: 29904236      PMCID: PMC5997287          DOI: 10.1055/s-0036-1590951

Source DB:  PubMed          Journal:  Synlett        ISSN: 0936-5214            Impact factor:   2.454


  17 in total

Review 1.  New catalytic approaches towards the enantioselective halogenation of alkenes.

Authors:  Ulrich Hennecke
Journal:  Chem Asian J       Date:  2012-02-07

2.  Enantioselective halocyclization reactions for the synthesis of chiral cyclic compounds.

Authors:  Guofei Chen; Shengming Ma
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-02       Impact factor: 15.336

3.  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

Review 4.  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

5.  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

6.  Catalytic, enantioselective, intramolecular carbosulfenylation of olefins. Preparative and stereochemical aspects.

Authors:  Scott E Denmark; Alex Jaunet
Journal:  J Org Chem       Date:  2013-12-11       Impact factor: 4.354

7.  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

8.  Catalytic, enantioselective, intramolecular carbosulfenylation of olefins.

Authors:  Scott E Denmark; Alex Jaunet
Journal:  J Am Chem Soc       Date:  2013-04-19       Impact factor: 15.419

9.  Catalytic asymmetric bromoetherification and desymmetrization of olefinic 1,3-diols with C2-symmetric sulfides.

Authors:  Zhihai Ke; Chong Kiat Tan; Feng Chen; Ying-Yeung Yeung
Journal:  J Am Chem Soc       Date:  2014-04-08       Impact factor: 15.419

10.  Catalytic, enantioselective, intramolecular carbosulfenylation of olefins. Mechanistic aspects: a remarkable case of negative catalysis.

Authors:  Scott E Denmark; Hyung Min Chi
Journal:  J Am Chem Soc       Date:  2014-02-18       Impact factor: 15.419

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  1 in total

1.  Flavin-dependent halogenases catalyze enantioselective olefin halocyclization.

Authors:  Dibyendu Mondal; Brian F Fisher; Yuhua Jiang; Jared C Lewis
Journal:  Nat Commun       Date:  2021-06-01       Impact factor: 14.919

  1 in total

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