Synthesis of chiral diaza-18-crown-6 derivatives from optically active diethanolamines

EFJ de Vries, P Steenwinkel, J Brussee…

Index: Vries, Erik F. J. de; Steenwinkel, Pablo; Brussee, Johannes; Kruse, Chris G.; Gen, Arne van der Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4315 - 4325

Full Text: HTML

Citation Number: 35

Abstract

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 ...