Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, Non-U.S. Gov’t, Journal of the American Chemical Society called Asymmetric reductive Mannich reaction to ketimines catalyzed by a Cu(I) complex, Author is Du, Yao; Xu, Li-Wen; Shimizu, Yohei; Oisaki, Kounosuke; Kanai, Motomu; Shibasaki, Masakatsu, which mentions a compound: 503538-69-0, SMILESS is FC1(F)OC2=CC=C(P(C3=CC=CC=C3)C4=CC=CC=C4)C(C5=C6OC(F)(F)OC6=CC=C5P(C7=CC=CC=C7)C8=CC=CC=C8)=C2O1, Molecular C38H24F4O4P2, Category: benzoxazole.
A highly diastereoselective reductive Mannich coupling of ketimines and α,β-unsaturated esters was developed using CuOAc-PPh3 or CuOAc-MePPh2 complex as a catalyst (5 mol %) and pinacolborane as a reducing reagent. The reaction was easily conducted at room temperature, and the substrate generality was broad. This platform methodol. was extended to the first catalytic asym. reductive Mannich reaction of ketimines using CuOAc-DIFLUORPHOS as the catalyst (10 mol %). Switching the reducing reagent from pinacolborane to (EtO)3SiH was key to inducing the high enantioselectivity (82-93% ee). High diastereoselectivity was also maintained (3:1∼30:1). Thus, products containing contiguous tetra- and trisubstituted carbons were catalytically synthesized with high stereoselectivities. Products were converted to α,β,β-trisubstituted (β2,3,3) amino acid derivatives without any racemization and epimerization through simple treatment under acidic conditions. This method is the first entry of the catalytic asym. synthesis of β2,3,3-amino acid derivatives, which constitute important chiral building blocks of biol. significant mols.
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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem