71056-40-1Relevant articles and documents
Iodide-Mediated Synthesis of Spirooxindolo Dihydrofurans from Iodonium Ylides and 3-Alkylidene-2-oxindoles
Laevens, Benjamin A.,Tao, Jason,Murphy, Graham K.
, p. 11903 - 11908 (2017)
An iodide-mediated reaction between cyclic iodonium ylides of 1,3-dicarbonyls and 3-alkylidene-2-oxindoles results in 3H-spiro[furan-2,3′-indolin]-2′-ones. The reaction was tolerant to substitutions on both the alkylidene and ylide substrates and provided
Catalytic enantioselective carboannulation with allylsilanes
Ball-Jones, Nicolas R.,Badillo, Joseph J.,Tran, Ngon T.,Franz, Annaliese K.
, p. 9462 - 9465 (2015/02/05)
The first catalytic asymmetric carboannulation with allylsilanes is presented. The enantioselective [3+2] annulation is catalyzed using a scandium(III)/indapybox complex with tetrakis-[3,5-bis(trifluoromethyl)phenyl]- borate (BArF) to enhance catalytic activity and control stereoselectivity. Functionalized cyclopentanes containing a quaternary carbon center are derived from alkylidene oxindole, coumarin, and malonate substrates with high stereoselectivity. The enantioselective 1,4-conjugate addition and enantioselective lactone formation (by trapping of the β-silyl carbocation) is also described. It's a trap: The catalytic asymmetric carboannulation of alkylidene oxindole, coumarin, and malonate substrates with allylsilanes in the presence of a ScIII/BArF/indapybox catalyst affords functionalized cyclopentanes containing a quaternary carbon center with high stereoselectivity. Enantioselective allylation and asymmetric lactone formation by trapping of the β-silyl carbocation are also presented.
