title: Stereocontrol in synthesis of homoallylic amines. Syn selective direct allylation of hydrazones with allylboronic acids.
abstract: Allylboronic acids directly react with acyl hydrazones, affording homoallylic amine derivatives. The reaction proceeds with very high syn selectivity, which is the opposite of the stereochemistry observed for allylboration of imines. The reaction can be carried out with both aromatic and aliphatic acyl hydrazones. Based on our studies the excellent syn stereochemistry can be explained by chelation control of the acyl hydrazone and the B(OH)(2) moiety.
authors.affiliation: Department of Organic Chemistry, ‡Department of Inorganic and Structural Chemistry, Stockholm University , SE-106 91 Stockholm, Sweden.
authors.forename: Arindam
authors.initials: A
authors.lastname: Das
authors.forename: Rauful
authors.initials: R
authors.lastname: Alam
authors.forename: Lars
authors.initials: L
authors.lastname: Eriksson
authors.forename: Kálmán J
authors.initials: KJ
authors.lastname: Szabó