title: Enantio- and diastereoselective organocatalytic α-alkylation of aldehydes with 3-substituted 2-(bromomethyl)acrylates.
abstract: The catalytic direct α-alkylation of aldehydes with 2-(bromomethyl)acrylates has been accomplished, giving rise to α-branched and functionalized aldehydes of high diastereo- and enantiopurity. The influence of the nature of the ester group of the acrylates in reaction stereoselectivity and especially in reactivity is investigated. Optimum conditions implicate the use of phenyl acrylates in conjunction with organocatalyst 8. Application of thus obtained adducts in synthesis is illustrated with a concise stereocontrolled preparation of trisubstituted cyclopentenes.
authors.affiliation: Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080, San Sebastián, Spain.
authors.forename: Jacqueline
authors.initials: J
authors.lastname: Jiménez
authors.forename: Aitor
authors.initials: A
authors.lastname: Landa
authors.forename: Aitziber
authors.initials: A
authors.lastname: Lizarraga
authors.forename: Miguel
authors.initials: M
authors.lastname: Maestro
authors.forename: Antonia
authors.initials: A
authors.lastname: Mielgo
authors.forename: Mikel
authors.initials: M
authors.lastname: Oiarbide
authors.forename: Irene
authors.initials: I
authors.lastname: Velilla
authors.forename: Claudio
authors.initials: C
authors.lastname: Palomo