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Ring-closing iodoamination of (E)-configured, N-α-methyl-p-methoxybenzyl protected homoallylic amines upon treatment with I 2 and NaHCO 3 in MeCN occurs with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give 3-iodopyrrolidines in >99:1 dr. This transformation was used as one of the key steps in the total asymmetric synthesis of (−)-codonopsinine, which was achieved...
The asymmetric synthesis of (−)-codonopsinine was achieved in 7 steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1dr. The key step in this synthesis involved ring-closing iodoamination of a functionalised homoallylic amine, which occurred with concomitant N-debenzylation, to give a 3-iodopyrrolidine that was elaborated to (−)-codonopsinine.
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