Chiral cyclic zwitterionic bipyridinium-4-olates for the diastereoselective synthesis of (R, S)- and (S, R)-trozamicol. Issue 15 (13th April 2016)

• Record Type: Journal Article
• Authors: López-González, Ricardo; Zárate, Araceli; Aparicio, David M.; Mendoza, Angel; Gnecco, Dino; Juárez, Jorge R.; Romero-Ceronio, Nancy; Orea, Laura; Terán, Joel L.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 15(2016)
• Page Start: 1683
• Page End: 1686
• Publication Date: 2016-04-13
• Subjects: Chiral cyclic zwitterionic -- Bipyridinium -- cis-3-Piperidinyl-4-hydroxypiperidines -- Trozamicol; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.03.029
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A practical synthesis of chiral cyclic zwitterionic bipyridinium olates is presented. Regiospecific synthesis of cis 4-hydroxy-3-piperidinyl piperidines. Total diastereoselective synthesis of ( R, S )- and ( S, R )-trozamicol. Abstract: A series of new chiral enantiopure cyclic zwitterionic bipyridinium-4-olates compounds were prepared in four steps starting from the corresponding primary chiral amine. With these intermediates, a convenient methodology has been developed for the synthesis of cis -3-piperidinyl-4-hydroxypiperidines. Specifically, the utility of this chiral zwitterionic type intermediate has been demonstrated by the synthesis of ( R, S )- and ( S, R )-trozamicol.