Regio- and Diastereoselective Cascade Reactions of Bicyclo[1.1.0]butanes: Access to gem-Difluorinated Carbocyclic Rings DOI
Zhiyi Zhang, Hao Wu, Wenjie Xu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 17, 2025

gem-Difluorinated carbocyclic rings are attractive motifs in drug development. Herein, we report the transition-metal free cascade reaction of bicyclo[1.1.0]butanes (BCBs) with gem-difluorocyclopropenes for synthesis gem-difluorinated excellent regio- and diastereoselectivity. This method was successfully applied to provide a broad range cyclopentenes cyclopropanes, which could undergo variety difluoromethylene (CF2) retaining transformations.

Language: Английский

Copper-Catalyzed Enantioselective [4π + 2σ] Cycloaddition of Bicyclobutanes with Nitrones DOI

Xuan-Ge Zhang,

Zi-Yang Zhou,

Jiaxin Li

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 25, 2024

The selective construction of bridged bicyclic scaffolds has garnered increasing attention because their extensive use as saturated bioisosteres arene in pharmaceutical industry. However, sharp contrast to racemic counterparts, assembling chiral structures an enantioselective and regioselective manner remains challenging. Herein, we describe our protocol for constructing 2-oxa-3-azabicyclo[3.1.1]heptanes (BCHeps) by [4π + 2σ] cycloadditions bicyclo[1.1.0]butanes (BCBs) nitrones taking advantage a copper(II) complex Lewis acid catalyst. This method features mild conditions, good functional group tolerance, high yield (up 99%), excellent enantioselectivity 99% ee). Density theory (DFT) calculation elucidates the origin reaction's mechanism BCB activation Cu(II) complex.

Language: Английский

Citations

17
Lewis-Acid-Catalyzed Dearomative [4π + 2σ] Cycloaddition of Bicyclobutanes with Isoquinolinium Methylides for the Synthesis of Ring-Fused Azabicyclo[3.1.1]heptanes DOI
Qin Jiang, Jianyang Dong,

Xuechen Zhou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9311 - 9315

Published: Oct. 17, 2024

Dearomative cycloadditions are valuable for efficiently generating three-dimensional molecular complexity. However, despite recent reports of bicyclobutanes (BCBs) the synthesis aza-bicyclo[3.1.1]heptanes (aza-BCHeps), which bioisosteres

Language: Английский

Citations

5
Regio- and Diastereoselective Cascade Reactions of Bicyclo[1.1.0]butanes: Access to gem-Difluorinated Carbocyclic Rings DOI
Zhiyi Zhang, Hao Wu, Wenjie Xu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 17, 2025

gem-Difluorinated carbocyclic rings are attractive motifs in drug development. Herein, we report the transition-metal free cascade reaction of bicyclo[1.1.0]butanes (BCBs) with gem-difluorocyclopropenes for synthesis gem-difluorinated excellent regio- and diastereoselectivity. This method was successfully applied to provide a broad range cyclopentenes cyclopropanes, which could undergo variety difluoromethylene (CF2) retaining transformations.

Language: Английский

Citations

0