6533b86dfe1ef96bd12c9316
RESEARCH PRODUCT
Aza-Henry Reaction of Isatin Ketimines with Methyl 4-Nitrobutyrate en Route to Spiro[piperidine-3,3′-oxindoles]
Gonzalo BlayM. Carmen MuñozMelireth HolmquistJosé R. Pedrosubject
chemistry.chemical_compoundNucleophilic additionNitroaldol reactionchemistryAmino estersStereochemistryIsatinNitroEnantioselective synthesisGeneral ChemistryPiperidineOximedescription
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 |
|---|---|---|---|---|
| 2015-12-04 | Advanced Synthesis & Catalysis |