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• W2027367026 abstract "(1R,2S)-Norephedrine has been employed in the synthesis of a novel 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one via reductive alkylation with acetone, N-nitrosation, reduction, and cyclization. The oxadiazinone was treated with either propionyl chloride or 3-thiophenylpropionyl chloride to afford the corresponding N3-acylated oxadiazinones 9a and 9b, respectively. X-ray crystallographic analysis of the N3-thiophenylpropionyl oxadiazinone 9b revealed that the C2-urethane carbonyl and the N3-carbonyl are arranged in an anti-periplanar conformation. The oxadiazinones were subsequently applied in the titanium-mediated asymmetric aldol addition reaction by treatment with titanium tetrachloride, triethylamine, and a variety of aldehydes at 0 °C. The aldol adducts 10a−i and 11a,b were found to have diastereoselectivities ranging from 8:1 to >99:1 favoring the formation of the non-Evans syn configuration. The absolute stereochemistry of the adduct 10a was determined by acid hydrolysis. This process afforded the N4-isopropyloxadiazinone 8 and (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoic acid 14 in ≥95% enantiomeric excess." @default.
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• W2027367026 date "2004-01-10" @default.
• W2027367026 modified "2023-10-03" @default.
• W2027367026 title "Intramolecular Chiral Relay at Stereogenic Nitrogen. Synthesis and Application of a New Chiral Auxiliary Derived from (1<i>R</i>,2<i>S</i>)-Norephedrine and Acetone" @default.
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• W2027367026 doi "https://doi.org/10.1021/jo035325n" @default.
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