title: Stereoselective synthesis of 1,3-anti diols by an Ipc-mediated domino aldol-coupling/reduction sequence.
abstract: A novel domino process for 1,3-anti diol synthesis by the union of a methyl ketone with an aldehyde is described. The operationally simple procedure is based on an Ipc-boron-aldol coupling and subsequent Ipc-mediated reduction of the intermediate β-hydroxy-ketone. The sequence proceeds with excellent anti-selectivities and enables the rapid construction of complex polyketide fragments.
authors.affiliation: Universität Heidelberg, Institut für Organische Chemie, INF 270, D-69120 Heidelberg, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Dieckmann
authors.forename: Dirk
authors.initials: D
authors.lastname: Menche
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D001895:Boron / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D007659:Ketones; C116609:3-hydroxybutanal; D001895:Boron