Chameleon Reactivity of the Allene Bond of 4-Vinylidene-2-oxazolidinone: Novel Through-Space Conjugative Nucleophilic Addition of Electron-Rich Alkenes and Hetero-Nucleophiles

• Published in: Chemistry : a European journal Vol. 13; no. 34; pp. 9686 - 9702
• Main Authors: Kimura, Masanari, Horino, Yoshikazu, Mori, Masahiko, Tamaru, Yoshinao
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.01.2007; WILEY‐VCH Verlag; Wiley
• Subjects: allenes; Chemistry; Chemistry, Multidisciplinary; Diels-Alder reactions; enols; indoles; Physical Sciences; Science & Technology; sulfonamides; COUPLING-CYCLIZATION REACTION; ACID; NITROGEN-HETEROCYCLES; ENOL ETHERS; EFFICIENT SYNTHESIS; FURAN-DIENE; sulfonamides; RADICAL CATALYZED ISOMERIZATION; 3+2 CYCLOADDITION; enols; Diels-Alder reactions; allenes; indoles; STEREOSELECTIVE-SYNTHESIS; DEMAND DIELS-ALDER

The CαCβ double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through‐space interaction with the NSO2 bond; the carbamate double bond is thus subject to nucleophilic addition for a wide variety of nucleophiles, which procee...