Phosphine-containing Lewis base catalyzed cyclization of benzofuranone type electron-deficient alkenes with allenoates: a facile synthesis of spirocyclic benzofuranones.
A regioselective [3 + 2] cycloaddition of benzofuranone type active olefins with allenoates catalyzed by trivalent phosphines has been developed, which provided an easy access to enriched functionalized spirocyclic benzofuranones. The reactions accommodated a number of benzofuranone type electron-deficient olefins and allenoates to give the desired 3-spirocyclopentane benzofuran-2-ones or 2-spirocyclopentane benzofuran-3-ones with moderate to excellent yields (up to 99%) and moderate to good regioselectivities (up to 11:1).
Department of Chemistry and State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, China. xin_li@nankai.edu.cn
Xin
X
Li
Feng
F
Wang
Nan
N
Dong
Jin-Pei
JP
Cheng
D000475:Alkenes / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D004583:Electrons; D007659:Ketones / Q000737:chemistry*; D058115:Lewis Bases / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D001572:Benzofurans; D007659:Ketones; D058115:Lewis Bases; D010720:Phosphines; D013141:Spiro Compounds; C044646:phosphine