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