title: Rapid access to polyketide scaffolds via vinylogous Mukaiyama aldol reactions.
abstract: [reaction: see text]. The use of the Z-configured vinylogous silyl ketene acetals in Mukaiyama aldol reactions is described. Isopropyl alcohol as scavanger and the use of tris(pentafluorophenyl)borane as the Lewis acid are required for obtaining the gamma-alkylated syn-product selectively. In cases of alpha-chiral aldehydes, Felkin-Anh selectivity was observed.
authors.affiliation: Institut für Organische Chemie der Universität Hannover, Schneiderberg 1B, D-30167 Hannover, Germany.
authors.forename: J
authors.initials: J
authors.lastname: Hassfeld
authors.forename: M
authors.initials: M
authors.lastname: Christmann
authors.forename: M
authors.initials: M
authors.lastname: Kalesse
mesh_terms: D019840:2-Propanol; D000080:Acetals / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D001880:Boranes; D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000447:Aldehydes; D001880:Boranes; D005030:Ethylenes; D007202:Indicators and Reagents; D007659:Ketones; C008223:ketene; D019840:2-Propanol