1059698-97-3Relevant academic research and scientific papers
Azine-N-oxides as effective controlling groups for Rh-catalysed intermolecular alkyne hydroacylation
Kalepu, Jagadeesh,Moseley, Daniel F.,Willis, Michael C.
, p. 13068 - 13073 (2021/10/21)
Heterocycle-derived aldehydes are challenging substrates in metal-catalysed hydroacylation chemistry. We show that by using azine N-oxide substituted aldehydes, good reactivity can be achieved, and that they are highly effective substrates for the intermolecular hydroacylation of alkynes. Employing a Rh(i)-catalyst, we achieve a mild and scalable aldehyde C-H activation, that permits the coupling with unactivated terminal alkynes, in good yields and with high regioselectivities (up to >20?:?1 l:b). Both substrates can tolerate a broad variety of functional groups. The reaction can also be applied to diazine aldehydes that contain a free N-lone pair. We demonstrate conversion of the hydroacylation products to the corresponding azine, through a one-pot hydroacylation/deoxygenation sequence. A one-pot hydroacylation/cyclisation, using N-Boc propargylamine, additionally leads to the synthesis of a bidentate pyrrolyl ligand.
Highly enantioselective Friedel-Crafts reaction of indoles with 2-enoylpyridine 1-oxides catalyzed by chiral pyridine 2,6-bis(5′,5′- diphenyloxazoline)-Cu(II) complexes
Singh, Pradeep K.,Singh, Vinod K.
supporting information; experimental part, p. 4121 - 4124 (2009/05/27)
(Chemical Equation Presented) The catalytic enantioselective Friedel-Crafts reaction of indoles with 2-enoylpyridine 1-oxides has been studied in the presence of chiral pyridine 2,6-bis(5′,5′-diphenyloxazoline)-Cu(II) complexes. The reaction furnished alk
