356762-89-5Relevant articles and documents
HFIP-mediated 2-aza-Cope rearrangement: Metal-free synthesis of α-substituted homoallylamines at ambient temperature
Gadde, Karthik,Maes, Bert U. W.,Abbaspour Tehrani, Kourosch
supporting information, p. 4067 - 4075 (2021/05/19)
An efficient metal-free strategy for the synthesis of α-substituted homoallylamine derivatives has been developed via a 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-promoted 2-aza-Cope rearrangement of aldimines, generated in situ by condensation of aldehydes with easily accessible 1,1-diphenylhomoallylamines. This reaction provides rapid access to α-substituted homoallylamines with excellent functional group tolerance and yields. The reaction takes place at room temperature and no chromatographic purification is required for product isolation. The synthetic utility of the current method is further demonstrated by the transformation of the obtained benzophenone ketimines into N-unprotected homoallylamines, an α-amino alcohol and an α-amino amide. This journal is
Copper-Catalyzed Umpolung of Imines through Carbon-to-Nitrogen Boryl Migration
Li, Zhenghua,Zhang, Liang,Nishiura, Masayoshi,Hou, Zhaomin
, p. 4388 - 4393 (2019/05/08)
We report a general strategy for the catalytic umpolung of imines, which was enabled by an unprecedented 1,2-boryl carbon-to-nitrogen migration. Based on the discovery of a rearrangement of an α-borylalkylamido copper intermediate to an α-borylaminoalkyl
Anti-Markovnikov Hydroamination of Homoallylic Amines
Ensign, Seth C.,Vanable, Evan P.,Kortman, Gregory D.,Weir, Lee J.,Hull, Kami L.
supporting information, p. 13748 - 13751 (2016/01/15)
The development of an anti-Markovnikov-selective hydroamination of unactivated alkenes is a significant challenge in organometallic chemistry. Herein, we present the rhodium-catalyzed anti-Markovnikov-selective hydroamination of homoallylic amines. The proximal Lewis basic amine serves to promote reactivity and enforce regioselectivity through the formation of the favored metallacycle, thus over-riding the inherent reactivity of the alkene. The scope of both the amine nucleophiles and homoallylic amines that participate in the reaction is demonstrated.