Exploring Diazo Compounds for the Divergent Electro-Cascade Sequence and S–H Insertion Reaction

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

Published: Feb. 12, 2025

We have explored the reactivity of diazo compounds under electrochemical conditions to establish a cascade sequence thiolation/cyclization/reduction reactions. Electrolyzing styryl imides and aryl thiols enables direct access single diastereoisomer 2,5-pyrrolidine-dione-fused thiochromans in good yield mild metal-free conditions. Notably, tunable has been achieved via S–H insertion at center modified reaction Based on experimental evidences, including detection key intermediates computational studies, mechanism for also established.

Language: Английский

Construction of dihydropyrano[2,3‐c]pyrazolone via photoinduced Wolff rearrangement/chiral isothiourea catalyzed [4+2] cyclization reaction

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(11)

Published: Aug. 13, 2024

Abstract A photoinduced Wolff rearrangement/chiral isothiourea catalyzed [4+2] cycloaddition reaction of pyrazolone derivatives and α ‐diazoketones was developed, affording the corresponding dihydropyrano[2,3‐ c ]pyrazolone in moderate to good yields (50–94 %) with satisfactory excellent diastereoselectivities (>20 : 1 dr, almost all cases) enantioselectivities 31–99 %. This protocol features readily available substrates, mild conditions, effective construction vicinal tertiary quaternary carbon stereocenters.

Language: Английский