title: Indium-mediated asymmetric Barbier-type allylation of aldimines in alcoholic solvents: synthesis of optically active homoallylic amines.
abstract: [reaction: see text] Chiral aldimines derived from phenylglycinol were diastereoselectively allylated with indium powder/allyl bromide in alcoholic solvents. Both aliphatic and aromatic aldimines provided good yield of the desired products with high diastereoselectivity. A racemization-free protocol for removal of the phenylglycinol auxiliary was also developed. The stereochemical assignment of the homoallylic amine was made by NMR spectroscopy and a transition state model was proposed to explain the selectivity.
authors.affiliation: Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Patumwan, Bangkok 10330, Thailand. vtirayut@chula.ac.th
authors.forename: Tirayut
authors.initials: T
authors.lastname: Vilaivan
authors.forename: Chutima
authors.initials: C
authors.lastname: Winotapan
authors.forename: Vorawit
authors.initials: V
authors.lastname: Banphavichit
authors.forename: Tetsuro
authors.initials: T
authors.lastname: Shinada
authors.forename: Yasufumi
authors.initials: Y
authors.lastname: Ohfune