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- Title
Direct Synthesis of Benzofuro[2,3- b]pyrroles through a Radical Addition/[3,3]-Sigmatropic Rearrangement/Cyclization/Lactamization Cascade.
- Authors
Ueda, Masafumi; Ito, Yuta; Ichii, Yuki; Kakiuchi, Maiko; Shono, Hiroko; Miyata, Okiko
- Abstract
A straightforward synthetic method for the construction of benzofuro[2,3- b]pyrrol-2-ones by a novel domino reaction through a radical addition/[3,3]-sigmatropic rearrangement/cyclization/lactamization cascade has been developed. The domino reaction of O-phenyl-conjugated oxime ether with an alkyl radical allows the construction of two heterocycles with three stereogenic centers as a result of the formation of two CC bonds, a CO bond, and a CN bond in a single operation, leading to pyrrolidine-fused dihydrobenzofurans, which are not easily accessible by existing synthetic methods. Furthermore, asymmetric synthesis of benzofuro[2,3- b]pyrrol-2-one derivatives through a diastereoselective radical addition reaction to a chiral oxime ether was also developed.
- Subjects
SIGMATROPIC rearrangements; CASCADE control; OXIMES; PYRROLIDINE; CHEMICAL reactions
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 22, p6763
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201402217