Cyclopent-2-enylaluminium as allylzinc precursor for the diastereoselective allylmetallation of non-racemic imines: applications to the synthesis of enantiomerically enriched heterocycles. Issue 1 (13th November 2015)

• Record Type: Journal Article
• Authors: Coffinet, Michaël; Lamy, Samantha; Jaroschik, Florian; Vasse, Jean-Luc
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 1(2016)
• Page Start: 69
• Page End: 73
• Publication Date: 2015-11-13
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02184g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A sequential titanium-catalyzed/hydroalumination/transmetallation/allylation of non-racemic imines which provides tunable homoallylamines for heterocyclic synthesis is presented. Abstract : The generation of cyclopent-2-enylzinc from cyclopentadiene based on a titanium-catalyzed hydroalumination/transmetallation sequence is described. Applied to the allylmetallation of phenylglycinol-derived imines, this sequence leads to homoallylic amines with moderate to good stereoselectivities. The synthesis of disubstituted azetidines and piperidines illustrates the potential of the method.