An asymmetric metal-templated route to amino acids with an isoquinolone core via a Rh(III)-catalyzed coupling of aryl hydroxamates with chiral propargylglycine Ni(II) complexes.

Autor: Arsenov MA; A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS), Vavilov Str. 28, 119991 Moscow, Russian Federation. dloginov@ineos.ac.ru., Stoletova NV; A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS), Vavilov Str. 28, 119991 Moscow, Russian Federation. dloginov@ineos.ac.ru., Savel'yeva TF; A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS), Vavilov Str. 28, 119991 Moscow, Russian Federation. dloginov@ineos.ac.ru., Smol'yakov AF; A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS), Vavilov Str. 28, 119991 Moscow, Russian Federation. dloginov@ineos.ac.ru.; Plekhanov Russian University of Economics, Stremyanny Per. 36, 117997 Moscow, Russian Federation., Maleev VI; A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS), Vavilov Str. 28, 119991 Moscow, Russian Federation. dloginov@ineos.ac.ru., Loginov DA; A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS), Vavilov Str. 28, 119991 Moscow, Russian Federation. dloginov@ineos.ac.ru.; Plekhanov Russian University of Economics, Stremyanny Per. 36, 117997 Moscow, Russian Federation., Larionov VA; A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS), Vavilov Str. 28, 119991 Moscow, Russian Federation. dloginov@ineos.ac.ru.; Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya Str. 6, 117198 Moscow, Russian Federation.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2022 Dec 07; Vol. 20 (47), pp. 9385-9391. Date of Electronic Publication: 2022 Dec 07.
DOI: 10.1039/d2ob01970a
Abstrakt: A general protocol for the asymmetric synthesis of artificial amino acids (AAs) comprising an isoquinolone skeleton was successfully elaborated via a straightforward Rh(III)-catalyzed C-H activation/annulation of various aryl hydroxamates with a series of robust chiral propargylglycine Ni(II) complexes derived from glycine (Gly), alanine (Ala) and phenylalanine (Phe) in a green solvent (methanol) under mild conditions (at room temperature under air). Notably, in the case of phenylalanine-derived complexes, the formation of unfavorable 4-substituted isoquinolone regioisomers was achieved by a catalyst control for the first time. The subsequent acidic decomposition of the obtained Ni(II) complexes provides the target unnatural α- and α,α-disubstituted AAs with an isoquinolone core in an enantiopure form.
Databáze: MEDLINE
Externí odkaz: