Liu, Hui; Yan, Yingkun; Li, Min; Zhang, Xiaomei published an article in 2021. The article was titled 《An enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived N-Boc ketimines》, and you may find the article in Organic & Biomolecular Chemistry.Electric Literature of C9H7NO The information in the text is summarized as follows:
By employing a chiral phosphoric acid as a catalyst, an enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived N-Boc ketimines was realized. The reaction provided a wide variety of novel 3-isoxazole 3-amino-oxindoles I (R1 = C6H5, 4-OMeC6H4, 4-FC6H4, etc.; R2 = Me, Et, Bn, Allyl; R3 = H, 5-Me, 5-Cl, etc.; R4 = H, Me, Et, Bn, Boc) with good yields (up to 99%) and moderate to good enantioselectivities (up to 99%). The absolute configuration of one product was assigned by X-ray crystal structural anal. and a plausible reaction mechanism was proposed. In addition, a scale-up reaction was performed successfully. Finally, one product was subjected to Suzuki-Miyaura coupling with phenylboronic acid to afford the product in a moderate yield without erosion of the enantioselectivity. The experimental process involved the reaction of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Electric Literature of C9H7NO)
3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used in the synthesis of substituted naphtho[1,8-bc]pyrans. It was also used as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics.Electric Literature of C9H7NO
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts