133007-27-9Relevant articles and documents
Reductive and oxidative transformations of the N-(cyanomethyl)oxazolidine system to expand the chiral pool of piperidines
Francois, David,Poupon, Erwan,Kunesch, Nicole,Husson, Henri-Philippe
, p. 4823 - 4829 (2007/10/03)
Two new reactions have been exploited to modify piperidine scaffolds containing the chiral, non-racemic N-(cyanomethyl)oxazolidine system. A Raney nickel mediated decyanation was studied first, followed by an oxidative process using potassium permanganate
An asymmetric synthesis of the key precursor to (-)-indolizomycin
Groaning, Michael D.,Meyers
, p. 4639 - 4642 (2007/10/03)
Using chiral bicyclic lactams, containing an α,β-unsaturation, the key precursor of (-)-indolizomycin was obtained in optically pure form. The sequence involved a >20:1 diastereoselective cyclopropanation of the unsaturated lactam 5 employing sulfoxonium methylide. TiCl4 mediated addition of allyltrimethylsilane afforded pyrrolidone 7 in a diastereomeric ratio of >20:1. The appropriately substituted pyrrolidone 2 was prepared by debenzylation and subsequent alkylation with 3-bromoproponic ester. The six step sequence from commercially available starting materials was performed in 26% overall yield.