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Synlett 1997; 1997(2): 171-172
DOI: 10.1055/s-1997-743
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An Improved Preparation of Oxazolidin-2-one Chiral Auxiliaries

Manjula Sudharshan, Philip G. Hultin*
  • *Department of Chemistry, University of Manitoba, Winnipeg Manitoba, Canada, R3T 2N2, Fax (204)-275-0905; hultin@cc.umanitoba.ca
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Publication History

Publication Date:
31 December 2000 (online)

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Reduction of carbamate-blocked amino esters by lithium borohydride (made in situ from sodium borohydride and lithium iodide) forms chiral 4-substituted oxazolidin-2-ones directly. The presence of iodide in the reaction mixture appears to promote the cyclization of the intermediate alkoxyborohydride. This provides a route to these important chiral auxiliaries, employing less hazardous reagents and simpler reaction conditions than do most existing methods.

α-amino ester - carbamate - lithium borohydride - iodide - oxazolidinone

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