1059698-88-2Relevant academic research and scientific papers
Chiral bipyridine-annulated bicyclo[3.3.1]nonane N-oxide organocatalysts for stereoselective allylation and hydrosilylation reactions
?eimyt?, Simona,Ston?ius, Sigitas
, (2021)
The synthesis of chiral C2-symmetric bis(bipyridine N,N′-dioxide) and bis(bipyridine N-monooxide) derivatives featuring bipyridine-annulated bicyclo[3.3.1]nonane framework is reported. The new Lewis basic bipyridine N,N′-dioxides exhibited good
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 Diastereo- and Enantioselective Michael Addition of Nitroalkanes to 2-Enoyl-Pyridine N-Oxides Catalyzed by Scandium(III)/Copper(II) Complexes
Li, Lijun,Zhang, Sheng,Hu, Yanbin,Li, Yanan,Li, Chong,Zha, Zhenggen,Wang, Zhiyong
, p. 12885 - 12888 (2015/09/07)
A C2-symmetric Schiff-base ligand, derived from tridentate-Schiff-base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2-enoyl-pyridine N-oxides. With this newly catalytic system, an unprecedented diastereoselectivity was obtained in the asymmetric Michael addition of nitroalkanes to 2-enoyl-pyridine N-oxides. In addition, a switch in enantioselectivity was achieved by using this newly catalytic system and our previous catalyst. After a facile reduction, the optically active adduct was converted to a biologically active dihydro-2H-pyrrol 4a. Furthermore, a connection of two tridentate-Schiff-base subunits proved to be an effective strategy in ligand design. Complex chemistry! A C2-symmetric Schiff-base ligand, derived from tridentate-Schiff-base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2-enoyl-pyridine N-oxides with unprecedented diastereoselectivity (see scheme).
N-Heterocyclic carbene-catalyzed diastereoselective synthesis of β-lactone-fused cyclopentanes using homoenolate annulation reaction
Mukherjee, Subrata,Mondal, Santigopal,Patra, Atanu,Gonnade, Rajesh G.,Biju, Akkattu T.
supporting information, p. 9559 - 9562 (2015/06/08)
NHC-catalyzed annulation of enals with 2-enoylpyridines or 2-enoylpyridine N-oxides leading to the diastereoselective synthesis of β-lactone-fused cyclopentanes is reported. The reaction proceeds via the generation of homoenolate equivalent intermediates and tolerates a broad range of functional groups.
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
