107836-65-7Relevant academic research and scientific papers
Catalytic diastereo- and enantioselective additions of versatile allyl groups to N-H ketimines
Jang, Hwanjong,Romiti, Filippo,Torker, Sebastian,Hoveyda, Amir H.
, p. 1269 - 1275 (2017)
There are many biologically active organic molecules that contain one or more nitrogen-containing moieties, and broadly applicable and efficient catalytic transformations that deliver them diastereoselectively and/or enantioselectively are much sought after. Various methods for enantioselective synthesis of α-secondary amines are available (for example, from additions to protected/activated aldimines), but those involving ketimines are much less common. There are no reported additions of carbon-based nucleophiles to unprotected/unactivated (or N-H) ketimines. Here, we report a catalytic, diastereo- and enantioselective three-component strategy for merging an N-H ketimine, a monosubstituted allene and B 2 (pin) 2, affording products in up to 95% yield, >98% diastereoselectivity and >99:1 enantiomeric ratio. The utility of the approach is highlighted by synthesis of the tricyclic core of a class of compounds that have been shown to possess anti-Alzheimer activity. Stereochemical models developed with the aid of density functional theory calculations, which account for the observed trends and levels of enantioselectivity, are presented.
Enantioselective hydrogenation of N-H imines
Hou, Guohua,Gosselin, Francis,Li, Wei,McWilliams, J. Christopher,Sun, Yongkui,Weisel, Mark,O'Shea, Paul D.,Chen, Cheng-Yi,Davies, Ian W.,Zhang, Xumu
supporting information; experimental part, p. 9882 - 9883 (2009/12/06)
(Figure Presented) N-H ketoimines 3a-3v are readily prepared in high yield via organometallic addition to nitriles and isolated as corresponding bench-stable hydrochloride salts. Homogeneous asymmetric hydrogenation of unprotected N-H ketoimines 3a-3v usi
Stereochemical and Mechanistic Aspects of the Base-catalysed Decomposition of N-Alkyloxaziridines to form NH Ketimines
Boyd, Derek R.,McCombe, Kenneth M.,Sharma, Narain D.
, p. 867 - 872 (2007/10/02)
The synthesis of a new range of oxaziridines (18)-(23), (30)-(35) by peracid oxidation of diaryl ketimines and aryl aldimines is reported.Relatively stable NH ketimine products (24)-(27) have been isolated from base-catalysed decomposition of the oxaziridines (18)-(20), (30)-(35) and a primary kinetic isotope effect (ca. kH/kD 6.0) was observed during decomposition of the oxaziridine trans-(31).The trans-oxaziridines (31)-(35) were found to decompose at a faster rate than the corresponding cis isomers.The relative rates of base-catalysed decomposition of oxaziridine stereoisomers are consistent with a mechanism involving an α-C-H proton abstraction mechanism.
