title: A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction.
abstract: A practical approach to highly functionalized 4-hydroxypyridine derivatives with stereogenic side chains in the 2- and 6-positions is described. The presented two-step process utilizes a multicomponent reaction of alkoxyallenes, nitriles and carboxylic acids to provide β-methoxy-β-ketoenamides which are transformed into 4-hydroxypyridines in a subsequent cyclocondensation. The process shows broad substrate scope and leads to differentially substituted enantiopure pyridines in good to moderate yields. The preparation of diverse substituted lactic acid derived pyrid-4-yl nonaflates is described. Additional evidence for the postulated mechanism of the multicomponent reaction is presented.
authors.affiliation: Freie Universität Berlin, Institut für Chemie und Biochemie, Takustr. 3, D-14195 Berlin, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Eidamshaus
authors.forename: Roopender
authors.initials: R
authors.lastname: Kumar
authors.forename: Mrinal K
authors.initials: MK
authors.lastname: Bera
authors.forename: Hans-Ulrich
authors.initials: HU
authors.lastname: Reissig