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Synthesis of chiral spiro 3-oxazolin-5-one 3-oxides (chiral nitrones) via a nitrosoketene intermediate and their asymmetric 1,3-dipolar cycloaddition reactions leading to the EPC synthesis of modified amino acids



Synthesis of chiral spiro 3-oxazolin-5-one 3-oxides (chiral nitrones) via a nitrosoketene intermediate and their asymmetric 1,3-dipolar cycloaddition reactions leading to the EPC synthesis of modified amino acids



Tetrahedron 53(16): 5725-5746



Cycloaddition of chiral cyclic ketones such as (-)-menthone, (+)-nopinone, and (+)- camphenilone to nitrosoketene generated by thermolysis of 5-hydroxyimino-2,2-dimethyl-1,3-dioxane-4,6-dione gave the corresponding chiral spiro 3-oxazolin-5-one 3-oxides (chiral cyclic nitrones). These corresponding oxazolidine derivatives with high diastereoselectivity, which were converted to optically pure amino acids.

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Accession: 009508418

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DOI: 10.1016/s0040-4020(97)00284-6


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