title: Diastereodivergent aldol reactions of beta-alkoxy ethyl ketones: modular access to (1,4)-syn and -anti polypropionates.
abstract: Asymmetric substrate-controlled aldol reactions of ethyl ketones of type 4 with aldehyde 3 are reported. Modular access to all possible syn- and anti-aldol products was obtained by careful choice of reaction conditions. To achieve good selectivities in this diastereodivergent approach, selection of the protective group on the beta-oxygen of the enolate (R (2)) was of critical importance.
authors.affiliation: University of Heidelberg, Department of Organic Chemistry, INF 270, 69120 Heidelberg, Germany.
authors.forename: Fatih
authors.initials: F
authors.lastname: Arikan
authors.forename: Jun
authors.initials: J
authors.lastname: Li
authors.forename: Dirk
authors.initials: D
authors.lastname: Menche
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D007659:Ketones; D011108:Polymers; D011422:Propionates; C116609:3-hydroxybutanal