175439-83-5Relevant academic research and scientific papers
Asymmetric Radical Process for General Synthesis of Chiral Heteroaryl Cyclopropanes
Deb, Arghya,Ke, Jing,Wang, Xiaoxu,Xu, Yijie,Zhang, X. Peter,Zhu, Yiling
supporting information, p. 11121 - 11129 (2021/08/03)
A highly efficient catalytic method has been developed for asymmetric radical cyclopropanation of alkenes with in situ-generated α-heteroaryldiazomethanes via Co(II)-based metalloradical catalysis (MRC). Through fine-tuning the cavity-like environments of newly-synthesized D2-symmetric chiral amidoporphyrins as the supporting ligand, the optimized Co(II)-based metalloradical system is broadly applicable to α-pyridyl and other α-heteroaryldiazomethanes for asymmetric cyclopropanation of wide-ranging alkenes, including several types of challenging substrates. This new catalytic methodology provides a general access to valuable chiral heteroaryl cyclopropanes in high yields with excellent both diastereoselectivities and enantioselectivities. Combined computational and experimental studies further support the underlying stepwise radical mechanism of the Co(II)-based olefin cyclopropanation involving α- and γ-metalloalkyl radicals as the key intermediates.
Alkylation of Aldehyde (Arenesulfonyl)hydrazones with Trialkylboranes
Kabalka, George W.,Maddox, John T.,Bogas, Ekaterini,Kelley, Shane W.
, p. 3688 - 3695 (2007/10/03)
(Arenesulfonyl)hydrazone derivatives of aryl aldehydes are readily alkylated by trialkylboranes in the presence of base to generate new organoboranes that may be converted to the corresponding substituted alkanes or alcohols depending upon the reaction conditions chosen. Both tosyl- and trisylhydrazone derivatives can be utilized in the reaction, which tolerates a variety of functional groups, making it a versatile alternative to both the Grignard and Suzuki-coupling reactions.
