Literature DB >> 25811099

Stereochemical studies of the opening of chloro vinyl epoxides: cyclic chloronium ions as intermediates.

Andrej Shemet1, David Sarlah1, Erick M Carreira1.   

Abstract

A systematic study of the opening of a collection of chlorinated vinyl epoxides is reported, which includes experiments that implicate both five- and four-membered chloronium ions as plausible intermediates in this type of epoxide opening reaction.

Entities:  

Year:  2015        PMID： 25811099     DOI： 10.1021/acs.orglett.5b00558

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


  4 in total

1.  Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Authors:  Matthew L Landry; Dennis X Hu; Grace M McKenna; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2016-04-08       Impact factor: 15.419

Review 2.  Stereoselective Halogenation in Natural Product Synthesis.

Authors:  Won-jin Chung; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

3.  Synthesis of malhamensilipin A exploiting iterative epoxidation/chlorination: experimental and computational analysis of epoxide-derived chloronium ions.

Authors:  J Saska; W Lewis; R S Paton; R M Denton
Journal:  Chem Sci       Date:  2016-08-02       Impact factor: 9.825

4.  Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers.

Authors:  J Boshkow; S Fischer; A M Bailey; S Wolfrum; E M Carreira
Journal:  Chem Sci       Date:  2017-08-09       Impact factor: 9.825
  4 in total

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