title: Diastereoselective synthesis of useful building blocks by crotylation of beta-branched alpha-methylaldehydes with potassium crotyltrifluoroborates.
abstract: The diastereoselective construction of stereotriads having consecutive methyl, hydroxy, and methyl substituents was realized by the substrate-controlled crotylation of beta-branched alpha-methylaldehydes with potassium crotyltrifluoroborates. Especially, crotylation of 2-(1,3-dithian-2-yl)propanal with potassium ( E)-crotyltrifluoroborate afforded, in good yield and with excellent diastereoselectivity, a useful building block that has different and potential functional groups on both ends.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Kyosuke
authors.initials: K
authors.lastname: Tanaka
authors.forename: Yukiko
authors.initials: Y
authors.lastname: Fujimori
authors.forename: Yoko
authors.initials: Y
authors.lastname: Saikawa
authors.forename: Masaya
authors.initials: M
authors.lastname: Nakata
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002073:Butanes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001881:Borates; D002073:Butanes; C005556:propionaldehyde