Direct Synthesis of Benzofuro[2, 3‐b]pyrroles through a Radical Addition/[3, 3]‐Sigmatropic Rearrangement/Cyclization/Lactamization Cascade. Issue 22 (27th March 2014)

• Record Type: Journal Article
• Authors: Ueda, Masafumi; Ito, Yuta; Ichii, Yuki; Kakiuchi, Maiko; Shono, Hiroko; Miyata, Okiko
• Is Part Of: Chemistry. Volume 20:Issue 22(2014)
• Page Start: 6763
• Page End: 6770
• Publication Date: 2014-03-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201402217
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A straightforward synthetic method for the construction of benzofuro[2, 3‐<italic>b</italic>]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 <italic>O</italic>‐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 CC bonds, a CO bond, and a CN 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‐<italic>b</italic>]pyrrol‐2‐one derivatives through a diastereoselective radical addition reaction to a chiral oxime ether was also developed.</p> </abstract>