Abstract
The synthesis of 2-functionalized 3,5-bis(hydroxymethyl)pyrrolidines from readily available polycyclic Diels-Alder adducts by a reaction sequence involving three steps is described. The same methodology has been applied to obtain the aziridine counterparts from the corresponding methyl 2-azatricyclo[3.2.1.02,4 ]oct-6-ene-4-carboxylates. The key steps in the synthetic strategy are dihydroxylation with osmium tetroxide/N -methylmorpholine N -oxide, oxidative cleavage with sodium periodate, and reduction using sodium borohydride or lithium aluminum hydride; overall yields ranged from 40-60%.
Keywords
asymmetric synthesis - cycloadditions - dihydroxylations - aziridinopyrrolidines - polyhydroxylated pyrrolidines
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