Abstract
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.
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