Intramolecular chiral relay at stereogenic nitrogen. Synthesis and application of a new chiral auxiliary derived from (1R,2S)-norephedrine and acetone.

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 N(3)-acylated oxadiazinones 9a and 9b… (More)

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Cite this paper

@article{Hitchcock2004IntramolecularCR, title={Intramolecular chiral relay at stereogenic nitrogen. Synthesis and application of a new chiral auxiliary derived from (1R,2S)-norephedrine and acetone.}, author={Shawn R. Hitchcock and David M. Casper and Jeremy F Vaughn and Jennifer M Finefield and Gregory M Ferrence and Joel M Esken}, journal={The Journal of organic chemistry}, year={2004}, volume={69 3}, pages={714-8} }