3319-04-8Relevant articles and documents
Dynamic kinetic resolution allows a highly enantioselective synthesis of cis-α-aminocycloalkanols by ruthenium-catalyzed asymmetric hydrogenation
Liu, Sheng,Xie, Jian-Hua,Wang, Li-Xin,Zhou, Qi-Lin
, p. 7506 - 7508 (2008/09/17)
(Chemical Equation Presented) Resolutely dynamic hydrogenation: A highly efficient asymmetric hydrogenation of racemic N,N-disubstituted α-aminocycloalkanones involving dynamic kinetic resolution in the presence of a ruthenium catalyst gives chiral α-aminocycloalkanols with excellent enantioselectivities and cis diastereoselectivities (see scheme). A synthesis of optically pure U-(-)-50488 based on this reaction is reported.
Efficient Preparation of Cis Vicinal Tertiary Diamines from 2-Hydroxy Ketones in Two Steps
Fraenkel, Gideon,Gallucci, Judith,Rosenzweig, Howard S.
, p. 677 - 681 (2007/10/02)
Cyclic (C5 and C6) cis vicinal tertiary diamines are efficiently prepared by catalytic hydrogenation, Pd(C), of the corresponding N-substituted amino enamines, e.g. 6.The latter are obtained by p-toluenesulfonic acid catalyzed condensation of secondary amines with cyclic 2-hydroxy ketones in refluxing benzene under Dean-Stark conditions or from the N-substituted 2-amino ketones.For example cis-1,2-dipyrrolidinocyclohexane has been obtained from adipoin in 69percent overall yield, isolated.