title: Asymmetric three-component domino reaction: an original access to chiral nonracemic 1,3-thiazin-2-ones.
abstract: A new asymmetric three-component domino process, based on a diastereoselective hetero-Diels-Alder reaction, involving an aldehyde, an alkene, and a chiral thiocarbamate was developed. The chiral auxiliary is directly removed during this process, leading to enantioenriched 2H-1,3-thiazin-2-ones with up to 96% ee.
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507 CNRS, INC3M, FR 3038, ENSICAEN, Université de Caen Basse Normandie , 6 Bd. Maréchal Juin, 14050 Caen, France , and Laboratoire d'Innovation Thérapeutique, UMR 7200 CNRS, Université de Strasbourg , Faculté de Pharmacie, 74 route du Rhin B.P. 24, 67401 Illkirch Cedex, France.
authors.forename: Flavie
authors.initials: F
authors.lastname: Peudru
authors.forename: Fabien
authors.initials: F
authors.lastname: Le Cavelier
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Lohier
authors.forename: Mihaela
authors.initials: M
authors.lastname: Gulea
authors.forename: Vincent
authors.initials: V
authors.lastname: Reboul
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D013237:Stereoisomerism; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000475:Alkenes; D013843:Thiazines