Synthesis of Fused-Housane Derivatives via Intramolecular [2 + 2] Photocycloaddition DOI

David Suárez‐García,

Miguel A. Rodrı́guez, Iratxe Barbolla

et al.

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

Published: April 9, 2025

Herein, we describe a [2 + 2] photocycloaddition of cyclopropenes bearing styryl group to prepare housane derivatives. The reaction occurs via selective excitation the styrene fragment, enabling completely stereoselective stepwise cycloaddition. Fused-housane derivatives with an unprecedented substitution pattern are prepared in simple manner using convenient visible light.

Language: Английский

Facile Synthesis of Housanes by an Unexpected Strategy DOI
Yanyao Liu,

Somanea Tranin,

Yu‐Che Chang

et al.

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

Published: Feb. 17, 2025

Rigid bicyclic hydrocarbons have emerged as important building blocks in the drug discovery industry. Despite progress this general area, bicyclo[2.1.0]pentanes (housanes) are an understudied class of molecules. Herein we report unconventional synthesis borylated housanes. Our method features a broad scope and high diastereoselectivities versatile intermediates. The route involves strain-release diboration bicyclo[1.1.0]butane intramolecular deborylative alkylation. versatility bridgehead boronic ester was demonstrated several functionalizations. Lastly, mechanism reaction investigated, unusual stereospecific diastereoselective ring expansion uncovered.

Language: Английский

Citations

2
Stereoselective Synthesis of Highly Functionalized Bicyclo[2.1.0]pentanes by Sequential [2 + 1] and [2 + 2] Cycloadditions DOI Creative Commons
Brockton Keen,

Christina Cong,

Alberto Castanedo

et al.

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

Published: Feb. 10, 2025

This study describes a method for the stereoselective synthesis of highly functionalized bicyclo[2.1.0]pentanes (housanes). The approach utilizes two-step sequence, silver- or gold-catalyzed cyclopropenation alkynes followed by an intermolecular [2 + 2] photocycloaddition reaction with electron-deficient alkenes. is established aryldiazoacetates. A regioselective cycloaddition cyclopropane was developed using blue LED irradiation, commercially available photocatalyst as triplet-sensitizer, and low temperature (−40 °C). diastereoselective, when enantioenriched cyclopropenes are used, it proceeds enantioretention.

Language: Английский

Citations

1
Synthesis of Fused-Housane Derivatives via Intramolecular [2 + 2] Photocycloaddition DOI

David Suárez‐García,

Miguel A. Rodrı́guez, Iratxe Barbolla

et al.

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

Published: April 9, 2025

Herein, we describe a [2 + 2] photocycloaddition of cyclopropenes bearing styryl group to prepare housane derivatives. The reaction occurs via selective excitation the styrene fragment, enabling completely stereoselective stepwise cycloaddition. Fused-housane derivatives with an unprecedented substitution pattern are prepared in simple manner using convenient visible light.

Language: Английский

Citations

0