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• W2952495079 abstract "Efficient preparation of enantiomerically pure (2S)-aziridine-2-carboxaldehyde 9 and its 2(R) isomer and highly diastereoselective addition of organolithium reagents to the aldehyde 9 are described. The diastereoselectivity in additions of the lithium reagents seems to come from chelation-controlled carbon-carbon bond formation and is influenced by the source of the organometallic compound, solvent, and the presence of a Li salt. The C(3)-N bond of the aziridine ring of the addition products was regioselectively reduced by catalytic hydrogenation in the presence of Pearlman's catalyst to provide enantiomerically pure 1,2-amino alcohols. The absolute stereochemistries of the amino alcohol 13a were assigned as (1S,2S) when the C-1 substituent was phenyl by comparison with those of commercially available norpseudoephedrine." @default.
• W2952495079 created "2019-06-27" @default.
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• W2952495079 date "1996-01-01" @default.
• W2952495079 modified "2023-10-03" @default.
• W2952495079 title "Efficient Synthesis of <i>Ephedra</i> Alkaloid Analogues Using an Enantiomerically Pure <i>N</i>-[(<i>R</i>)-(+)-α-Methylbenzyl]aziridine-2-carboxaldehyde" @default.
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• W2952495079 doi "https://doi.org/10.1021/jo9603183" @default.
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