921589-65-3Relevant academic research and scientific papers
Diastereo- and enantioselective addition of anilide-functionalized allenoates to N-acylimines catalyzed by a pyridylalanine-based peptide
Mbofana, Curren T.,Miller, Scott J.
, p. 3285 - 3292 (2014)
A selective peptide-catalyzed addition of allenic esters to N-acylimines is reported. Tetrasubstituted allenes were achieved with up to 42:1 diastereomeric ratio and 94:6 enantiomeric ratio (up to 99:1 er after recrystallization of the major diastereomer). An exploration of the role of individual amino acids within the peptide was undertaken. The scope of the reaction was explored and revealed heightened reactivity with thioester-containing allenes. A mechanistic framework that may account for the observed reactivity is also described.
One-pot catalytic enantioselective synthesis of tetrahydropyridines via a nitro-mannich/hydroamination cascade
Barber, David M.,Sanganee, Hitesh J.,Dixon, Darren J.
supporting information, p. 5290 - 5293 (2013/01/15)
The highly enantioselective preparation of synthetically useful tetrahydropyridine derivatives employing a one-pot nitro-Mannich/hydroamination cascade is reported. This approach utilizes an asymmetric organocatalytic nitro-Mannich reaction followed by a gold-catalyzed alkyne hydroamination/ isomerization sequence that yields the desired tetrahydropyridines in good yields and high diastereo- and enantioselectivities.
Bismuth triflate-catalyzed addition of allylsilanes to N- alkoxycarbonylamino sulfones: Convenient access to 3-Cbz-protected cyclohexenylamines
Ollevier, Thierry,Li, Zhiya
supporting information; experimental part, p. 3251 - 3259 (2010/04/24)
Bismuth triflate was found to be an efficient catalyst in the Sakurai reaction of allyltrimethylsilanes with N-alkoxycarbonylamino sulfones. The reaction proceeded smoothly with a low catalyst loading of Bi(OTf) 3·4H2O (2-5 mol%) to afford the corresponding protected homoallylic amines in very good yields (up to 96%). A sequential allylation reaction followed by ring-closing metathesis delivers 6-8 membered 3-Cbz-protected cycloalkenylamines.
