Kinetic resolution of allylic alcohols promoted by electrophilic selenium reagents
The first example of a kinetic resolution process promoted by an electrophilic selenium reagent 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 (98% de). The unreacted alcohol can be recovered in a optically enriched form (92% ee). Copyright Taylor & Francis Inc.
A chiral electrophilic selenium reagent to promote the kinetic resolution of racemic allylic alcohols
(Chemical Equation Presented) 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).
Tiecco, Marcello,Testaferri, Lorenzo,Santi, Claudio,Tomassini, Cristina,Bonini, Rosaria,Marini, Francesca,Bagnoli, Luana,Temperini, Andrea
p. 4751 - 4753
(2007/10/03)
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