A chiral electrophilic selenium reagent to promote the kinetic resolution of racemic allylic alcohols.
[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).
Tiecco
Marcello
M
Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, Italy. tiecco@unipg.it
Testaferri
Lorenzo
L
Santi
Claudio
C
Tomassini
Cristina
C
Bonini
Rosaria
R
Marini
Francesca
F
Bagnoli
Luana
L
Temperini
Andrea
A