title: Synthesis of 1,2-amino alcohols by sigmatropic rearrangements of 3-(N-tosylamino)allylic alcohol derivatives.
abstract: Sigmatropic rearrangements of 3-(N-tosylamino)allylic alcohol derivatives, a particular subclass of functionalized enamides, have been investigated. Whereas the presence of the nitrogen atom alters the stereochemical outcome of Ireland-Claisen rearrangements of glycolates derived from such substrates, [2,3]-Wittig rearrangements of α-allyloxy acetamides or propargylic ethers derivatives provide access to a wide variety of functionalized 1,2-amino alcohols usually with high levels of stereocontrol, as well as to heterocyclic compounds. The stereoselectivity issues of these rearrangements (1,2-diastereoselectivity, auxiliary-induced diastereoselection, chirality transfer, and double stereodifferentiation) were thoroughly investigated.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS (UMR 7084), 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Marion
authors.initials: M
authors.lastname: Barbazanges
authors.forename: Christophe
authors.initials: C
authors.lastname: Meyer
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
authors.forename: Peter
authors.initials: P
authors.lastname: Turner
mesh_terms: D000577:Amides / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000605:Amino Alcohols