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Direct Synthesis of Benzofuro[2,3‐ b ]pyrroles through a Radical Addition/[3,3]‐Sigmatropic Rearrangement/Cyclization/Lactamization Cascade
Author(s) -
Ueda Masafumi,
Ito Yuta,
Ichii Yuki,
Kakiuchi Maiko,
Shono Hiroko,
Miyata Okiko
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402217
Subject(s) - chemistry , sigmatropic reaction , cascade reaction , stereocenter , domino , pyrrolidine , cascade , ether , medicinal chemistry , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , chromatography
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.