216754-42-6Relevant articles and documents
Transition-metal free C-C bond cleavage/borylation of cycloketone oxime esters
Zhang, Jin-Jiang,Duan, Xin-Hua,Wu, Yong,Yang, Jun-Cheng,Guo, Li-Na
, p. 161 - 166 (2019)
An efficient transition-metal free C-C bond cleavage/borylation of cycloketone oxime esters has been described. In this reaction, the B2(OH)4 reagent not only served as the boron source but also acted as an electron donor source through formation of a complex with a DMAc-like Lewis base. This complex could be used as an efficient single electron reductant in other ring-opening transformations of cycloketone oxime esters. Free-radical trapping, radical-clock, and DFT calculations all suggest a radical pathway for this transformation.
gamma-hydroxy unsaturated nitriles: chelation-controlled conjugate additions.
Fleming,Wang,Steward
, p. 1477 - 1479 (2000)
[reaction--see text] Chelation between gamma-hydroxy unsaturated nitriles and Grignard reagents promotes an otherwise difficult anionic conjugate addition reaction. The intermediate chelate is readily generated by deprotonation with t-BuMgCl followed by the addition of a second Grignard reagent that triggers an intramolecular conjugate addition. Structurally diverse Grignard reagents add with equal efficiency, providing an intermediate anion that stereoselectively alkylates BnBr in an overall addition-alkylation reaction.