666736-25-0Relevant academic research and scientific papers
A new look at boron enolate chemistry: Aminative C-C bond formation using diaminoboron enolate with aldehyde
Suginome, Michinori,Uehlin, Lars,Yamamoto, Akihiko,Murakami, Masahiro
, p. 1167 - 1169 (2004)
Unlike ordinary boron enolates, such as dialkylboryl (R2B) and dialkoxyboryl ((RO)2B) derivatives, reactions of diaminoboryl ((R2N)2B) enolates with aldehydes proceed with the concurrent transfer of amino and enoxy groups from the boron to the aldehyde carbon, yielding β-amino ketones in a selective manner.
Synthesis and structural characterization of the bis(diisopropylamino)boron enolate of tert-butyl methyl ketone
Ma, Lili,Hopson, Russell,Li, Deyu,Zhang, Yong,Williard, Paul G.
, p. 5834 - 5839 (2008/10/09)
Lithium, sodium, and potassium enolates reacted with bisaminoboron halides to give bisaminoboron enolates 1a-5c. Specifically, the potassium enolate of tert-butyl methyl ketone reacted with bis-(diisopropylamino)boron chloride in THF at room temperature within 1h to give the bis(diisopropylamino)-boron enolate of tert-butyl methyl ketone (3b) in 61-84% isolated yields. Under similar conditions, the reactivity is highly dependent on the metal employed to generate enolates (K > Na > Li) as well as the nitrogen substituents in the bisaminoboron halides (iPr > Et > TMS). This latter observation is a compromise between the boron-nitrogen resonance and the steric effect. The structural information of enolate 3b was studied in detail. Unlike the aggregated alkali-metal enolates, this boron enolate exists exclusively as a monomer in both the solid and solution states, as identified by X-ray and diffusion-ordered NMR.
