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).
A Chiral Electrophilic Selenium Reagent to Promote the Kinetic Resolution of Racemic Allylic Alcohols
TIECCO, Marcello;TESTAFERRI, Lorenzo;SANTI, Claudio;TOMASSINI, Cristina;MARINI, Francesca;BAGNOLI, Luana;TEMPERINI, Andrea
2004
Abstract
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).File in questo prodotto:
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