4.7 Article

A practical and efficient route for the highly enantioselective synthesis of mexiletine analogues and novel β-thiophenoxy and pyridyl ethers

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 17, Pages 6928-6931

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo801181d

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Funding

  1. National Institutes of Health [GM 08216]
  2. INBRE [NC P20 RR-016470]

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A practical and efficient procedure for the enantioselective synthesis of mexiletine analogues with use of 10% of spiroborate ester 6 as chirality transfer agent is presented. A variety of mexiletine analogues were prepared in good yield with excellent enantioselectivities (91-97% ee) from readily available starting materials. The developed methodology was also successfully applied for the synthesis of novel beta-amino ethers containing thiophenyl and pyridyl fragments.

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