Highly Enantioselective Organocatalytic Mannich Reaction of α-Benzylidene Succinimides with N-Boc Imines: Experimental and Theoretical Studies DOI

K Kimura,

Yuto Shimizu,

Katsuya Kanno

и другие.

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

Опубликована: Март 24, 2025

The development of efficient and practical methods for the construction chiral succinimide frameworks, which are backbone various natural products widely studied in field pharmaceuticals, attracts considerable research attention. In this study, an asymmetric Mannich reaction α-benzylidene succinimides with N-Boc imines was successfully performed using a bifunctional squaramide-type organocatalyst derived from quinine, affording corresponding adduct two contiguous stereocenters high yields (up to 98%) diastereoselectivities >20:1 dr) excellent enantioselectivities 99% ee). This protocol provides direct approach prepare derivatives simple starting material. Density Functional Theory (DFT) calculations conformational search autosampling program revealed that enantioselectivity profile dominated by deformation organocatalyst.

Язык: Английский

Chiral phosphoric acid-catalyzed atroposelective oxidative coupling of carbazoles DOI
Lu Qian,

Minjie Bi,

Yong‐Bin Wang

и другие.

Science China Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 14, 2025

Язык: Английский

Процитировано

0
Highly Enantioselective Organocatalytic Mannich Reaction of α-Benzylidene Succinimides with N-Boc Imines: Experimental and Theoretical Studies DOI

K Kimura,

Yuto Shimizu,

Katsuya Kanno

и другие.

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

Опубликована: Март 24, 2025

The development of efficient and practical methods for the construction chiral succinimide frameworks, which are backbone various natural products widely studied in field pharmaceuticals, attracts considerable research attention. In this study, an asymmetric Mannich reaction α-benzylidene succinimides with N-Boc imines was successfully performed using a bifunctional squaramide-type organocatalyst derived from quinine, affording corresponding adduct two contiguous stereocenters high yields (up to 98%) diastereoselectivities >20:1 dr) excellent enantioselectivities 99% ee). This protocol provides direct approach prepare derivatives simple starting material. Density Functional Theory (DFT) calculations conformational search autosampling program revealed that enantioselectivity profile dominated by deformation organocatalyst.

Язык: Английский

Процитировано

0