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

Авторы: Arsenov Mikhail A., Stoletova Nadezhda V., Savel’yeva Tat’yana F., Smol’yakov Alexander F., Maleev Victor I., Loginov Dmitry A., Larionov Vladimir A.
Журнал: Organic and Biomolecular Chemistry
Том: 20
Номер: 47
Год издания: 2022
Издательство: Royal Society of Chemistry
Местоположение издательства: United Kingdom
Первая страница: 9385
Последняя страница: 9391
DOI: 10.1039/D2OB01970A
Аннотация: A general protocol for the asymmetric synthesis of artificial amino acids (AAs) comprising an isoquinolone skeletal 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 green solvent (methanol) and under mild conditions (at room temperature under air atmosphere). 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.
Добавил в систему: Ларионов Владимир Анатольевич

	ИСТИНА	Войти в систему Регистрация
	ФНКЦ РР
	Главная Поиск Статистика О проекте Помощь

ИСТИНА