title: Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids.
abstract: The first examples of highly enantioselective [2,3]-sigmatropic rearrangements of acyclic allylic ammonium ylids are reported. Thus, a range of N-{2'-[(N'-allyl-N',N'-dialkyl)ammonium]}acetyl camphor sultams undergo rearrangement at 0 degrees C in DME solution with high diastereofacial control (up to 99:1 dr) to give allylglycines in generally high yield. The power of the method has been demonstrated in a rapid and efficient synthesis of (R)-allyl glycine.
authors.affiliation: School of Chemistry, University of Reading, Reading RG6 6AD, UK, and Hoffmann-La Roche, Ltd., Discovery Chemistry, 4070-Basel, Switzerland.
authors.forename: James A
authors.initials: JA
authors.lastname: Workman
authors.forename: Neil P
authors.initials: NP
authors.lastname: Garrido
authors.forename: Julien
authors.initials: J
authors.lastname: Sançon
authors.forename: Edward
authors.initials: E
authors.lastname: Roberts
authors.forename: Hans Peter
authors.initials: HP
authors.lastname: Wessel
authors.forename: J B
authors.initials: JB
authors.lastname: Sweeney
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D000501:Allylglycine / Q000138:chemical synthesis / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D000644:Quaternary Ammonium Compounds; D000501:Allylglycine; D005998:Glycine