Construction of chiral chroman skeletons via catalytic asymmetric [4+2] cyclization of ortho-hydroxyphenyl-substituted para-quinone methides catalyzed by a chiral-at-metal rhodium complex was written by Yang, Jian;Ming, Siliang;Yao, Gang;Yu, Haifeng;Du, Yu;Gong, Jun. And the article was included in Organic Chemistry Frontiers in 2022.Formula: C6H8N2O This article mentions the following:
An efficient asym. [4+2] cyclization of α,β-unsaturated 2-acyl imidazoles I (R1 = Me, iso-Pr, phenyl; R2 = Ph, 2-naphthyl, 1-methyl-1H-indol-3-yl, etc.) with ortho-hydroxyphenyl-substituted para-quinone methide derivatives II (R3 = H, 3-fluoro, 4-Me, 5-methoxy, etc.) catalyzed by a chiral-at-metal rhodium complex III has been developed. Enantioenriched chroman derivatives bearing three contiguous tertiary stereocenters IV (R4 = H, 6-methoxy, 7-Me, 8-fluoro, etc.) were obtained in generally high yields (up to 97%) and good stereoselectivities (up to >20:1 dr, >99% ee). This reaction represents the first catalytic asym. [4+2] cyclization of ortho-hydroxyphenyl-substituted p-QMs using chiral Lewis acids as catalysts, which will enrich the field of the catalytic asym. reactions of p-QM derivatives More importantly, it also provides a useful method for constructing chiral chroman skeletons. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Formula: C6H8N2O).
1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Formula: C6H8N2O
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem