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