Tetrahedron p. 7037 - 7044 (1996)
Update date:2022-08-04
Topics: Synthesis Diastereoselectivity Lewis acid Yield Reactivity Nucleophile Electrophile Stereochemistry Characterisation
Ince, Julie
Ross, Tracey M.
Shipman, Michael
Slawin, Alexandra M.Z.
Ennis, David S.
N-triphenylmethyl-2-methyleneaziridine 8 was synthesized from N-(2-bromo-2-propenyl)-amine 7 by treatment with sodium amide in liquid ammonia and its structure established using x-ray crystallography. Using modified conditions, (S)-N-(1-phenylethyl)-2-methyleneaziridine 9 was prepared in enantiomerically enriched form. Studies directed towards the synthesis of N-tosyl and N-Boc methyleneaziridines 14 and 15 respectively reveal limitations with this methodology.
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