《Stereodivergent Asymmetric Synthesis of α,β-Disubstituted β-Aminoalkylboronic Acid Derivatives via Group-Selective Protodeboronation Enabling Access to the Elusive Anti Isomer》 was published in Journal of the American Chemical Society in 2020. These research results belong to Li, Xiangyu; Hall, Dennis G.. Quality Control of Bis[(pinacolato)boryl]methane The article mentions the following:
Chiral β-aminoalkylboronates generate growing interest as versatile synthetic building blocks to access β-aminoalcs. and other useful compounds, and also as bioisosteres of β-amino acids in drug discovery. In this study, the lack of methodol. to access both syn and anti diastereomers of optically enriched, acyclic α,β-disubstituted β-aminoalkylboronates is addressed with the development of a divergent, diastereoselective strategy for the monoprotodeboration of β-amino gem-bis(boronate) precursors. To this end, new reaction conditions were successfully optimized to provide the elusive anti diastereomer by inverting a sequence of desulfinylation and protodeboronation. The desired syn or anti isomers are isolated independently in good yields and excellent diastereoselectivity (up to >20:1 dr) for a wide scope of substituents. The diastereotopic group selectivity of the new conditions yielding the anti isomer is rationalized by invoking a reactive rotamer featuring two ammonium-boronate hydrogen bonds, which enables phosphate coordination to boron with a concomitant, stereoretentive protonation of the C-B bond. The accessibility and utility of both diastereomers of these α,β-disubstituted β-aminoalkylboronates is exemplified with the functionalization of the amino group, stereospecific oxidation to β-amino alcs. and C-C bond transformations of the secondary alkylboronate, and the preparation of free boronic acids and hemiboronic heterocycles. After reading the article, we found that the author used Bis[(pinacolato)boryl]methane(cas: 78782-17-9Quality Control of Bis[(pinacolato)boryl]methane)
Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Quality Control of Bis[(pinacolato)boryl]methane Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.
Referemce:
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