1029702-01-9Relevant academic research and scientific papers
Improving carbene-copper-catalyzed asymmetric synthesis of α-aminoboronic esters using benzimidazole-based precursors
Wen, Kun,Wang, Han,Chen, Jinbo,Zhang, He,Cui, Xiaodan,Wei, Chao,Fan, Erkang,Sun, Zhihua
, p. 3405 - 3409 (2013/06/26)
By using a benzimidazole core and N-substitutions to tune the electronic properties of the corresponding N-heterocyclic carbenes, a one-pot protocol for efficient synthesis of α-aminoboronic esters without the need of a glovebox was developed in this work. The starting materials for the transformation can also be extended from aldehydes to ketones. An alternative protocol with short reaction time using preformed carbene-copper chloride is also described.
Metal free catalytic hydroboration of multiple bonds in methanol using N-heterocyclic carbenes under open atmosphere
Wen, Kun,Chen, Jinbo,Gao, Feng,Bhadury, Pinaki S.,Fan, Erkang,Sun, Zhihua
, p. 6350 - 6356 (2013/09/23)
An easy to operate method of catalytic hydroboration of unsaturated compounds has been developed with wide substrate scope. Reactions of various aldimines, ketimines, α,β-unsaturated carbonyl compounds, and alkynes were successfully executed with bis(pinacolato)diboron and N-heterocyclic carbenes in methanol without requiring a transition metal or inert atmosphere.
Asymmetric copper-catalyzed synthesis of α-amino boronate esters from N-tert-butanesulfinyl aldimines
Beenen, Melissa A.,An, Chihui,Ellman, Jonathan A.
, p. 6910 - 6911 (2008/12/22)
A general and efficient new method for the asymmetric synthesis of α-amino boronate esters has been developed. The key step is the Cu(I)-catalyzed addition of bis(pinacolato)diboron to N-tert-butanesulfinyl aldimines, which proceeds in good yields (52-88%) and with very high diastereoselectivities (>96:2) for a variety of aldimine substrates. This method was applied to an efficient synthesis of bortezomib, a potent α-amino boronic acid inhibitor of the proteasome that is in clinical use for the treatment of multiple myeloma and mantle cell lymphoma. Copyright
