18700-21-5Relevant articles and documents
Second-Generation palladium catalyst system for transannular C-H functionalization of azabicycloalkanes
Cabrera, Pablo J.,Lee, Melissa,Sanford, Melanie S.
supporting information, p. 5599 - 5606 (2018/05/03)
This article describes the development of a second-generation catalyst system for the transannular C-H functionalization of alicyclic amines. Pyridine- and quinoline-carboxylate ligands are shown to be highly effective for increasing the reaction rate, yield, and scope of Pd-catalyzed transannular C-H arylation reactions of azabicyclo[3.1.0]hexane, azabicyclo[3.1.1]heptane, azabicyclo[3.2.1]octane, and piperidine derivatives. Mechanistic studies reveal that the pyridine/quinoline-carboxylates play a role in impeding both reversible and irreversible catalyst decomposition pathways. These ligands enable the first reported examples of the transannular C-H arylation of the ubiquitous tropane, 7-azanorbornane, and homotropane cores. Finally, the pyridine/quinoline-carboxylates are shown to promote both transannular C-H arylation and transannular C-H dehydrogenation on a homotropane substrate.
Synthesis of exo- and endo-6,7-epoxytropanes
Justice, David E.,Malpass, John R.
, p. 11963 - 11976 (2007/10/03)
Diastereoisomeric N-protected 2,3-epoxy-4-amino-cycloheptanols are synthesised; cyclisation of derivatives provides a practical route to N-protected exo-(β)-6,7-epoxynortropanes and the first endo-(α-)-6,7-epoxynortropane. Hydride reduction gives the corr
Exo- and Endo-6-Hydroxy- and 6,7-Epoxytropanes; Total Synthesis of Scopine, Pseudoscopine, and Nor- Derivatives
Justice, David E.,Malpass, John R.
, p. 4689 - 4692 (2007/10/02)
Novel endo- 6,7-epoxy-8-azabicyclooctane derivatives and the corresponding exo-analogues have been synthesised and show substantially different reactivity; the resistance of the exo-epoxides to ring opening during hydride reduction and catalytic hydrogenolysis is exploited in a total synthesis of scopine, pseudoscopine, and nor- derivatives.