150125-85-2Relevant academic research and scientific papers
Synthesis of Chiral Diaza-18-crown-6 Derivatives from Optically Active Diethanolamines
Vries, Erik F. J. de,Steenwinkel, Pablo,Brussee, Johannes,Kruse, Chris G.,Gen, Arne van der
, p. 4315 - 4325 (2007/10/02)
Homotopic 1,10-diaza-18-crown-6 derivatives with two, four, and six chiral centers have been prepared in optically active form from diethanolamines via a cyclization reaction with tosylates 39 and 48.The requisite optically active diethanolamines were prepared from chiral cyanohydrins and chiral ethanolamines by a one-pot Grignard-transimination-reduction or a one-pot reduction-transimination-reduction procedure.Yields were strongly affected by the size of the substituents α to the nitrogen atom.The stereoselectivity of the diethanolamine synthesis was found to depend on the configuration of the ethanolamine used.
