6533b826fe1ef96bd12845ac
RESEARCH PRODUCT
ChemInform Abstract: Aza-Henry Reaction of Isatin Ketimines with Methyl 4-Nitrobutyrate en Route to Spiro[piperidine-3,3′-oxindoles].
Gonzalo BlayMelireth HolmquistJosé R. PedroM. Carmen Muñozsubject
chemistry.chemical_compoundNitroaldol reactionchemistryAmino estersIsatinNitroEnantioselective synthesisGeneral MedicinePiperidineOximeMedicinal chemistryAdductdescription
A new enantioselective route to spiro[piperidine-3,3′-oxindoles] from isatin ketimines is described. The aza-Henry reaction of N-Boc-isatin ketimines with methyl 4-nitrobutyrate in the presence of a Ph2BOX-CuBr2 complex provided the corresponding nitro amino esters with good diastereoselectivity and excellent enantioselectivity (up to >99% ee). The aza-Henry adducts were transformed into spiro[piperidine-3,3′-oxindoles] after reduction of the nitro group to oxime, and cleavage of the N-Boc group and lactamisation.
year | journal | country | edition | language |
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2016-04-01 | ChemInform |