Chiral β‐Lactams by Ruthenium‐Catalyzed Enantioselective CH Carbene Insertion DOI

Anna Lena Opper,

Xin Nie, Sergei I. Ivlev

и другие.

European Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 16, 2025

A ruthenium‐catalyzed intramolecular carbenoid insertion into a C(sp 3 )  H bond leads to the enantioselective formation of chiral β‐lactams. The reaction is catalyzed by ruthenium complex featuring pyridine‐2,6‐bis(oxazoline) ligand, combined with cyclometalated phenylimidazo[1,5‐ ]pyridine ligand. This belongs recently introduced new class catalysts ( Angew. Chem. Int. Ed. 2020 , 59 12393). Starting from N ‐benzyl α‐diazoacetamides, β‐lactams are provided in up 82% isolated yield 98% enantiomeric excess, without any occurrence Buchner side reaction. Mechanistic experiments reveal that β‐lactam (4‐membered ring) inherently favored over more common γ‐lactam (5‐membered formation.

Язык: Английский

Chiral β‐Lactams by Ruthenium‐Catalyzed Enantioselective CH Carbene Insertion DOI

Anna Lena Opper,

Xin Nie, Sergei I. Ivlev

и другие.

European Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 16, 2025

A ruthenium‐catalyzed intramolecular carbenoid insertion into a C(sp 3 )  H bond leads to the enantioselective formation of chiral β‐lactams. The reaction is catalyzed by ruthenium complex featuring pyridine‐2,6‐bis(oxazoline) ligand, combined with cyclometalated phenylimidazo[1,5‐ ]pyridine ligand. This belongs recently introduced new class catalysts ( Angew. Chem. Int. Ed. 2020 , 59 12393). Starting from N ‐benzyl α‐diazoacetamides, β‐lactams are provided in up 82% isolated yield 98% enantiomeric excess, without any occurrence Buchner side reaction. Mechanistic experiments reveal that β‐lactam (4‐membered ring) inherently favored over more common γ‐lactam (5‐membered formation.

Язык: Английский

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