Azanorbornadienes as Thiol-Reactive Cleavable Linkers | Zendy

Lucrezia De Pascalis | Zendy; Srinivas Tekkam | Zendy; M. G. Finn | Zendy

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Azanorbornadienes as Thiol-Reactive Cleavable Linkers

Author(s) -

Lucrezia De Pascalis,

Srinivas Tekkam,

M. G. Finn

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c01912

Subject(s) - chemistry , thiol , furan , cleavage (geology) , conjugate , pyrrole , michael reaction , oxidative cleavage , combinatorial chemistry , reactive intermediate , stereochemistry , organic chemistry , catalysis , mathematical analysis , geotechnical engineering , mathematics , fracture (geology) , engineering

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.

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