Simple exploration of Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate

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Generation and Cycloadditions of 4,5-Dihydrooxazole- and Oxazolidine-4-carbonitrile N-Oxides

A route to 2-phenyl-4,5-dihydrooxazole-4-carbonitrile N-oxide 7 has been developed starting from (S)-serine methyl ester and involving dehydration of the 4-nitromethyl derivative 13 using m-tolylene diisocyanate and triethylamine.Cycloaddition of the nitrile oxide to styrene afforded a 55:45 mixture of diastereoisomeric dihydroisoxazoles 21 and 22; furazan N-oxides 19 and 20 were also formed in a competing dimerisation.The analogous (R)-oxazolidine-4-carbonitrile oxide 8, also prepared from (S)-serine methyl ester, reacted similarly with styrene, oct-1-ene and diethyl fumarate to afford ca. 1:1 mixtures of adducts.The structures of the dihydrooxazole-dihydroisoxazole adduct 21 and furazan N-oxide 20 were determined by X-ray crystallography.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2492NO – PubChem