Asymmetric Construction of Chiral 2‐Azetines and Axially Chiral Tetrasubstituted Allenes via Phosphine Catalysis DOI Open Access
Yi Tang, Mingxia Huang,

Jingrong Jin

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Abstract Chiral 2‐azetines and allenes are highly valuable structural units in natural products useful chemicals. However, enantioselective synthesis of both has been extremely challenging. Herein, we present asymmetric construction chiral (70–98 % yields up to 96 ee) through phosphine‐catalyzed [2+2] annulation yne‐enones with sulfamate‐derived cyclic imines. These were easily transformed into upon treatment Et 3 SiH, BF ⋅ 2 O water at rt for minutes. Based on the above transformations, a concise one‐pot synthetic procedure combining imines under phosphine catalysis sequential reduction/isomerization/ring‐opening reaction was thus set up, providing axially tetrasubstituted satisfactory enantioselectivities (56–90 91 ee).

Language: Английский

Asymmetric Construction of Chiral 2‐Azetines and Axially Chiral Tetrasubstituted Allenes via Phosphine Catalysis DOI Open Access
Yi Tang, Mingxia Huang,

Jingrong Jin

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Chiral 2-azetines and allenes are highly valuable structural units in natural products useful chemicals. However, enantioselective synthesis of both has been extremely challenging. Herein, we present asymmetric construction chiral (70-98 % yields up to 96 ee) through phosphine-catalyzed [2+2] annulation yne-enones with sulfamate-derived cyclic imines. These were easily transformed into upon treatment Et

Language: Английский

Citations

1
Asymmetric Construction of Chiral 2‐Azetines and Axially Chiral Tetrasubstituted Allenes via Phosphine Catalysis DOI Open Access
Yi Tang, Mingxia Huang,

Jingrong Jin

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Abstract Chiral 2‐azetines and allenes are highly valuable structural units in natural products useful chemicals. However, enantioselective synthesis of both has been extremely challenging. Herein, we present asymmetric construction chiral (70–98 % yields up to 96 ee) through phosphine‐catalyzed [2+2] annulation yne‐enones with sulfamate‐derived cyclic imines. These were easily transformed into upon treatment Et 3 SiH, BF ⋅ 2 O water at rt for minutes. Based on the above transformations, a concise one‐pot synthetic procedure combining imines under phosphine catalysis sequential reduction/isomerization/ring‐opening reaction was thus set up, providing axially tetrasubstituted satisfactory enantioselectivities (56–90 91 ee).

Language: Английский

Citations

0