Practical synthesis of fluorous oxazolidinone chiral auxiliaries from alpha-amino acids |
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Authors: | Hein Jason E Geary Laina M Jaworski Ashley A Hultin Philip G |
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Institution: | Department of Chemistry, University of Manitoba, Winnipeg, MB, R3T 2N2, Canada. |
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Abstract: | reaction: see text] A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral alpha-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture. |
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