Oxazine formation by MsCl/Et3N as a convenient tool for the stereochemical interconversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Asymmetric synthesis of N-acetyl l-xylo- and l-arabino-phytosphingosines |
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Authors: | Om V. Singh |
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Affiliation: | Department of Chemistry, The University of Texas at San Antonio, 6900 N. Loop 1604 West, San Antonio, TX 78249, USA |
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Abstract: | Use of MsCl/Et3N was proven to provide a convenient synthetic tool for the stereochemical intercoversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Thus, under these conditions, the alcohols 4 and 6 smoothly converted to the oxazines 5 and 7, respectively, which were hydrolyzed to generate the corresponding inverted alcohols 6 and 4 in one pot. Further elaboration of 4 and 6 led to the efficient asymmetric synthesis of N-acetyl l-xylo- and l-arabino-phytosphingosines (11 and 15), respectively, via olefin cross metathesis reactions. |
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Keywords: | Phytosphingosine Regioselective asymmetric aminohydroxylation Olefin cross metathesis Oxazine |
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