Synthesis of chiral oxazolidin-2-ones from N-alkoxycarbonyl amino epo...

http://pubs.rsc.org/en/content/articlelanding/2002/p1/b203702e

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Issue 14, 2002Perkin Transactions 1 ceased publication in 2002. Organic & Biomolecular Chemistry is the RSC's journal for high-quality, original organic chemistry research. Journal Home Paper

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Synthesis of chiral oxazolidin-2-ones from N-alkoxycarbonyl amino epo...

http://pubs.rsc.org/en/content/articlelanding/2002/p1/b203702e

F. Javier Casado-Bellver,a M. Eugenia Gonzlez-Rosende,*b Amparo Asensio,a J. Miquel JordGregori,a Angeles Alvarez-Sorolla,a Jos Seplveda-Arques,*b Mario Orenac and Roberta Galeazzi*c Show Affiliations
J. Chem. Soc., Perkin Trans. 1, 2002, 1650-1654

DOI: 10.1039/B203702E Received 17 Apr 2002, Accepted 30 May 2002 First published online 24 Jun 2002 More| | | | | | PDF Rich HTML Add PDF to Basket (36) Download Citation Request Permissions

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Synthesis of chiral oxazolidin-2-ones from N-alkoxycarbonyl amino epo...

http://pubs.rsc.org/en/content/articlelanding/2002/p1/b203702e

threo-N-Alkoxycarbonylamino epoxides 5ad, containing the oxazolidine moiety, were converted into trans-4,5-disubstituted-2-oxazolidin-2-ones 2 with total regio- and stereoselection by means of nucleophilic intramolecular attack of the carbamate moiety to the protonated oxirane ring. Theoretical calculations confirmed both the regioselection and the preference of the cyclocarbamation reaction vs. the intermolecular attack by the solvent, arising from different behaviour in comparison with the analogous iodonium ions.

F. Javier CasadoBellver M. Eugenia GonzlezRosende Amparo Asensio J. Miquel JordGregori Angeles AlvarezSorolla Jos Seplveda-Arques Mario Orena Roberta Galeazzi

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4/15/2014 10:15 AM

Synthesis of chiral oxazolidin-2-ones from N-alkoxycarbonyl amino epo...

http://pubs.rsc.org/en/content/articlelanding/2002/p1/b203702e

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4/15/2014 10:15 AM

Synthesis of chiral oxazolidin-2-ones from N-alkoxycarbonyl amino epo...

http://pubs.rsc.org/en/content/articlelanding/2002/p1/b203702e

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