title: Stereodivergent addition of 4-silyloxy-1,2-allenes to aldehydes by hydroboration.
abstract: All-ene one! Three out of four stereoisomers of 2-vinyl-1,3-diols can be obtained from a single allene. A simple variation of the reaction conditions modifies the stereochemical outcome of the addition of an allene to an aldehyde via hydroboration. Stereocontrol is dependent upon the order in which the reagents are mixed (leading to E or Z boron species) and the type of aldehyde (aliphatic or aromatic) used.
authors.affiliation: Departament de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB (IBUB), Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona, Spain.
authors.forename: Carolina
authors.initials: C
authors.lastname: Sánchez
authors.forename: Xavier
authors.initials: X
authors.lastname: Ariza
authors.forename: Josep
authors.initials: J
authors.lastname: Cornellà
authors.forename: Jaume
authors.initials: J
authors.lastname: Farràs
authors.forename: Jordi
authors.initials: J
authors.lastname: Garcia
authors.forename: Jordi
authors.initials: J
authors.lastname: Ortiz
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D001895:Boron / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000466:Alkadienes; D020005:Propanols; C006463:allyl alcohol; C025947:propadiene; D001895:Boron