Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines: stereoselective synthesis of a d-ribo-phytosphingosine derivative |
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Authors: | Jongho Jeon |
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Institution: | Department of Chemical and Biological Engineering, Seoul National University, Seoul 151-744, Republic of Korea |
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Abstract: | Protection of 1,2-dialkyl substituted (Z)-allylic amines with an N,N-diBoc group resulted in an opposite stereoselectivity in the OsO4-catalyzed dihydroxylation reactions to that of N-Boc-(Z)-allylic amines. A higher anti selectivity (>10:1) was shown in CH2Cl2. An efficient stereoselective synthesis of a tetraacetyl derivative of d-ribo-phytosphingosine was reported using the N,N-diBoc-controlled dihydroxylation from Garner’s aldehyde. |
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