Details

Autor(en) / Beteiligte

• De Pascalis, Lucrezia
• Tekkam, Srinivas
• Finn, M.G

Titel

Azanorbornadienes as Thiol-Reactive Cleavable Linkers

Ist Teil von

• Organic letters, 2020-08, Vol.22 (16), p.6248-6251

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2020

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Azanorbornadienes (ZNDs), prepared from pyrroles, undergo Michael reaction with thiols followed by retro-Diels–Alder (rDA) cleavage to release the starting pyrrole and a thiomaleate. Somewhat less reactive in this regard than furan-derived oxanorbornadienes, ZNDs have an additional point of variability at the pyrrole nitrogen center. Sulfonylated ZNDs were far more stable toward rDA cleavage than acylated analogues. tert-Butoxycarbonyl examples were much less reactive with thiols, rendering the rDA step slower than the initial conjugate addition.