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Pyrrolidines from β-Aminoselenides via Radical Cyclization. Diastereoselectivity Control by the N-Substituent
journal contribution
posted on 2000-05-02, 00:00 authored by Magnus Besev, Lars EngmanN-Allyl-β-aminoalkyl phenyl selenidesprecursors of 3-aza-5-hexenyl radicalswere prepared by ring opening of N-allylaziridines with
benzeneselenol under acidic conditions or by sodium cyanoborohydride reduction of N-allylimines of α-phenylselenenyl ketones. The effect
of various N-protective groups (acyl, sulfonyl, or phosphinoyl) on diastereoselectivity in thermally or photochemically initiated 3-aza-5-hexenyl
reductive radical cyclization was studied. Whereas N-unprotected derivatives afforded trans-2,4-disubstituded pyrrolidines with good selectivity,
the diphenylphosphinoyl group directed cyclization to occur in a highly cis-selective manner.
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tranderivativePyrrolidineradicaldiphenylphosphinoyl groupdiastereoselectivityphotochemicallyAminoselenidemannerallylaziridinesulfonyldisubstitudedphenylselenenylAllylpyrrolidineRadical Cyclizationcyclizationacidic conditionsallyliminereductiveacylsodium cyanoborohydride reductionDiastereoselectivity Controlselenideazaketonering openingbenzeneselenol
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