(matrix presented) A two-step approach for the diastereoselective synthesis of 4-carboxymethyl 5-alkyl/aryl oxazolidin-2-ones is described, which proceeds via the intermediate formation of 2-carboxymethyl 3-alkyl/aryl N-tert-butoxycarbonyl (N-Boc) aziridines. By reaction of N-Boc β-amino methyl esters with LiHMDS and iodine, trans 2,3-disubstituted N-Boc aziridines are obtained with high stereoselectivities and yields. The final rearrangement to oxazolidin-2-ones is achieved by treatment with a catalytic amount of a Lewis acid and proceeds with high yield and complete regio- and stereoselectivity.
Novel synthesis of 4-carboxymethyl 5-alkyl/aryl oxazolidin-2-ones by rearrangement of 2-carboxymethyl 3-alkyl/aryl N-tert-butoxycarbonyl aziridines / Tomasini C.; Vecchione A.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 1:13(1999), pp. 2153-2156. [10.1021/ol991225l]
Novel synthesis of 4-carboxymethyl 5-alkyl/aryl oxazolidin-2-ones by rearrangement of 2-carboxymethyl 3-alkyl/aryl N-tert-butoxycarbonyl aziridines
Tomasini C.
;
1999
Abstract
(matrix presented) A two-step approach for the diastereoselective synthesis of 4-carboxymethyl 5-alkyl/aryl oxazolidin-2-ones is described, which proceeds via the intermediate formation of 2-carboxymethyl 3-alkyl/aryl N-tert-butoxycarbonyl (N-Boc) aziridines. By reaction of N-Boc β-amino methyl esters with LiHMDS and iodine, trans 2,3-disubstituted N-Boc aziridines are obtained with high stereoselectivities and yields. The final rearrangement to oxazolidin-2-ones is achieved by treatment with a catalytic amount of a Lewis acid and proceeds with high yield and complete regio- and stereoselectivity.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
