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. 2008 Sep 5;73(17):6928-31.
doi: 10.1021/jo801181d. Epub 2008 Aug 9.

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

Kun Huang  1 , Margarita Ortiz-Marciales, Viatcheslav Stepanenko, Melvin De Jesús, Wildeliz Correa
Affiliations

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

Kun Huang et al. J Org Chem. .

Abstract

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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Figures

Figure 1
Figure 1
Mexiletine and examples of its more potent analogues.
Figure 2
Figure 2
Spiroborate esters derived from nonracemic aminoalcohols and ethylene glycol.
Figure 3
Figure 3
Neuronal nicotinic acetylcholine receptors agonist.
Scheme 1
Scheme 1
Synthetic Route to 12a
See this image and copyright information in PMC

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