DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9322 - 9327

Published: Oct. 24, 2024

The present work develops a DMAP-catalyzed [3 + 2] cycloaddition of vinyl oxiranes with activated ketone compounds, affording dioxolane derivatives moderate to excellent yields. This approach represents the first Lewis base (LB)-catalyzed ring-opening reaction epoxides, simultaneously providing rare oxygen-containing active intermediate in this field. gram-scale preparation and facile derivatization cycloadduct highlight significant synthetic potential strategy.

Language: Английский

Synthesis of Indole‐Fused Eight‐Membered Oxa‐Rings via Palladium‐Catalyzed Asymmetric [4+4] Cycloaddition of Indole‐2,3‐Quinodimethanes with 2‐Alkylidenetrimethylene Carbonates

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 16, 2024

Comprehensive Summary We report a palladium‐catalyzed asymmetric [4+4] cycloaddition reaction between 2‐alkylidenetrimethylene carbonate and electron‐deficient indole‐2,3‐quinodimethanes ( IQDMs ). This features exclusive regioselectivity, high yield (up to 98%), excellent enantioselectivity 95% ee), easy scale‐up without any loss of efficiency, making it valuable for the synthesis indole‐fused eight‐membered oxa‐rings.

Language: Английский