Keto boronate reduction: a novel method for high 1,3-relative asymmetric induction

Photoelectrochemical oxidative C(sp3)−H borylation of unactivated hydrocarbons

“…The regioselectivity seems to be very sensitive to the carbonyl group, with no borylation observed at its α-position in all the cases. When the use of pentan-2-one ( 40 ) and heptan-4-one ( 41 ) was investigated under the standard conditions, the corresponding products can be obtained without obvious preference (β:γ = 50:50), probably due to an effect of boron–carbonyl-oxygen interaction 83 , 84 . Likewise, the C(sp 3 )–H borylation of 2-methylpentan-3-one ( 42 ) gave no preference to the β- and β’-positions.…”

Complexes based on alkylboranes and ,-unsaturated carbonyl compounds as bicomponent transfer agents for free-radical polymerisation

“…The existence of a complex involving each of them and methyl vinyl ketone ( 1 ) was first checked using 11 B NMR analyses as in the case of 1 ‐ 2 5. The formation of such a complex formation (Table 7) was only observed for the 7 ‐ 1 couple, with a strong chemical shift of 11 B. Mollander14 obtained the same result at low temperature when studying the formation of complexes between carbonyl compounds and alkyl borinate compounds that he used to carry out stereoselective reactions. Such complexes have only been observed by X‐ray analyses 15…”

Synthesis and Structural Investigation of Internally Coordinated α-Amidoboronic Acids

“…A plausible explanation for the reduced cyclization rate of these boroSar inhibitors is the formation of an intramolecular five-membered (:OC−N−C−B) ring structure in which the carbonyl oxygen atom coordinates to the boron, effectively stabilizing the active trans conformer of the dipeptide. Such intramolecular five-membered-ring motifs with a B−O dative bond have been observed in esters derived from boronic acids, − and postulated as intermediates in the stereoselective reduction of neighboring carbonyl groups. − However, relatively little is known about the factors associated with the formation of these intramolecular (:OC−N−C−B) rings, or their influence on the therapeutic efficacy of potential drugs. It should be mentioned that the presence of intramolecular B−N dative bonds has been correlated to some unexpected physiological behavior. − …”

“…Such intramolecular fivemembered-ring motifs with a B-O dative bond have been observed in esters derived from boronic acids, 25-27 and postulated as intermediates in the stereoselective reduction of neighboring carbonyl groups. [28][29][30] However, relatively little is known about the factors associated with the formation of these intramolecular (:OdC-N-C-B) rings, or their influence on the therapeutic efficacy of potential drugs. It should be mentioned that the presence of intramolecular B-N dative bonds has been correlated to some unexpected physiological behavior.…”