Stereocontrolled Synthesis of Cyclobutylamines Enabled by Lewis Acid-Catalyzed (3 + 2 + 2) Cycloaddition/Ring-Opening Strategy of Bicyclo[1.1.0]butanes with Triazinanes DOI

Yijun Duan,

Feng Chen,

Ye Guo

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

Herein, we develop a modular and efficient "cycloaddition/ring-opening" strategy of bicyclo[1.1.0]butanes (BCBs) with triazinanes to provide series syn-diastereoselective cyclobutylamines via 2,4-diazabicyclo[4.1.1]octanes (aza-BCOs). The reaction features simple operation, mild conditions, broad substrate scope. Mechanistic studies suggest that the cycloaddition follows stepwise (3 + 2 2) rather than (4 3) cycloaddition, involving an SN2 nucleophilic addition formaldimine Lewis acid-activated BCB species. A scale-up experiment various synthetic transformations product further highlight utility. We expect our findings will encourage exploration chemistry access more synthetically challenging cyclobutane frameworks.

Language: Английский

Enantioselective Synthesis of Tetrahydro-1H-1,3-methanocarbazoles by Formal (3 + 3)-Cycloaddition Using Bicyclo[1.1.0]butanes DOI
Shubham Dutta, Constantin G. Daniliuc, Christian Mück‐Lichtenfeld

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

Asymmetric synthesis presents many challenges, with the selective formation of chiral bridged polyheterocycles being a notable example. Cycloadditions using bicyclo[1.1.0]butanes (BCB) offer promising solution along those lines, yet, despite significant advances in that emerging area, asymmetric control has remained limited thus far. Here, we describe an organocatalytic, enantioselective formal (3 + 3)-cycloaddition BCBs 1H-indol-3-yl((hetero)aryl)methanol derivatives. This approach enables rapid and efficient tetrahydro-1H-1,3-methanocarbazole derivatives (34 examples) from readily available starting materials, very good stereochemical (up to 98:2 er). Successful scale-up experiments product modification demonstrated potential this methodology. Control DFT calculations provide insights into mechanistic pathway.

Language: Английский

Citations

4
Titanocene dichloride-catalyzed synthesis of heterocycles accelerated by in-situ formed Lewis and Brønsted acids DOI
Yuanyong Yao,

Li Tu,

Xiu Wang

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 573, P. 114822 - 114822

Published: Jan. 18, 2025

Language: Английский

Citations

0
Lewis Acid-Catalyzed Enantioselective (4 + 3)/Thia-(3 + 2) Cycloadditions of Bicyclobutanes and Enaminothiones: Catalyst-Directed Divergent Synthesis of Bridged Sulfur Heterocycles DOI
Lei Tang,

Wenjuan Bai,

Keqing Wang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7877 - 7890

Published: April 28, 2025

Language: Английский

Citations

0
Stereocontrolled Synthesis of Cyclobutylamines Enabled by Lewis Acid-Catalyzed (3 + 2 + 2) Cycloaddition/Ring-Opening Strategy of Bicyclo[1.1.0]butanes with Triazinanes DOI

Yijun Duan,

Feng Chen,

Ye Guo

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

Herein, we develop a modular and efficient "cycloaddition/ring-opening" strategy of bicyclo[1.1.0]butanes (BCBs) with triazinanes to provide series syn-diastereoselective cyclobutylamines via 2,4-diazabicyclo[4.1.1]octanes (aza-BCOs). The reaction features simple operation, mild conditions, broad substrate scope. Mechanistic studies suggest that the cycloaddition follows stepwise (3 + 2 2) rather than (4 3) cycloaddition, involving an SN2 nucleophilic addition formaldimine Lewis acid-activated BCB species. A scale-up experiment various synthetic transformations product further highlight utility. We expect our findings will encourage exploration chemistry access more synthetically challenging cyclobutane frameworks.

Language: Английский

Citations

3