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Org Lett. 2004 Dec 9;6(25):4751-3.

A chiral electrophilic selenium reagent to promote the kinetic resolution of racemic allylic alcohols.

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  • 1Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Universit√† di Perugia, Italy. tiecco@unipg.it

Abstract

[reaction: see text] The first example of a kinetic resolution process promoted by electrophilic selenium reagents is reported. Racemic allylic alcohols react with half equivalents of a selenenylating agent in methanol leading to the regiospecific formation of the corresponding addition products with a very high level of facial selectivity (from 95:5 to 98:2 dr). The unreacted alcohols can be recovered in an optically enriched form (from 90 to 94% ee).

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