title: Syn-selective vinylogous Kobayashi aldol reaction.
abstract: The Kobayashi aldol reaction has become a prominent transformation in polyketide syntheses. This methodology takes advantage of the directing effects of the Evans auxiliary and allows the stereoselective incorporation of a four carbon segment with two additional methyl branches establishing an anti-relationship between the two newly formed chiral centers. So far this transformation was restricted to anti-aldol products. We present here a modified protocol that provides the corresponding aldol product with high syn-selectivity.
authors.affiliation: Institut für Organische Chemie and Centre of Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany.
authors.forename: Gerrit
authors.initials: G
authors.lastname: Symkenberg
authors.forename: Markus
authors.initials: M
authors.lastname: Kalesse
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D010080:Oxazoles; D061065:Polyketides; C116609:3-hydroxybutanal