Novel stereoselective synthesis of functionalized oxazolidinones from chiral aziridines

Chan Sun Park, Min Sung Kim, Taebo Sim, Do Kyu Pyun, Cheol Hae Lee, Daeock Choi, Won Koo Lee, Jae Won Chang, Hyun Joon Ha

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Abstract

Enantiomerically pure N-(R)-α-methylbenzyl-4(R)-(chloromethyl)oxazolidinones (4R)-5a-k were synthesized in one step and high yields from various aziridine-2-methanols (S)-2a-k by intramolecular cyclization with phosgene. The α-methylbenzyl substituent on the nitrogen was easily cleaved to give both enanatiomers of 4-(chloromethyl)oxazolidinones (R)-7a and (S)-7a. (R)-7a was used for the efficient syntheses of (L)-homophenylalaninol analogues (S)-12a-j. We also applied the same methodology to prepare oxazolidinones 9a-c containing a heteroatom-substituted alkyl group at C-4 in high yields.

Original languageEnglish
Pages (from-to)43-49
Number of pages7
JournalJournal of Organic Chemistry
Volume68
Issue number1
DOIs
Publication statusPublished - 2003 Jan 10
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Park, C. S., Kim, M. S., Sim, T., Pyun, D. K., Lee, C. H., Choi, D., Lee, W. K., Chang, J. W., & Ha, H. J. (2003). Novel stereoselective synthesis of functionalized oxazolidinones from chiral aziridines. Journal of Organic Chemistry, 68(1), 43-49. https://doi.org/10.1021/jo025545l