title: (E)-alpha-substituted gamma-alkoxyallylboronic esters as new reagents: synthesis and reactivity toward aldehydes.
abstract: We have developed a synthesis of new allylboration reagents based on an allylic rearrangement. This approach led to the alpha-substituted gamma-alkoxyallylboronates 2 with a high stereoselectivity in favor of the E-isomer, independent of the organometallic used. We have also studied the reactivity of these reagents toward aldehydes, showing that the allylboration reaction occurs with an excellent diastereoselectivity to give the anti-diol derivatives 5. Moreover, the sequence can be carried out in a "one-pot" procedure avoiding the purification of allylboronates.
authors.affiliation: Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France.
authors.forename: Françoise
authors.initials: F
authors.lastname: Possémé
authors.forename: Michael
authors.initials: M
authors.lastname: Deligny
authors.forename: François
authors.initials: F
authors.lastname: Carreaux
authors.forename: Bertrand
authors.initials: B
authors.lastname: Carboni