Synthesis of 1-deoxy-D-galactohomonojirimycin via enantiomerically pure allenylstannanes |
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| Authors: | Achmatowicz Michal Hegedus Louis S |
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| Affiliation: | Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA. |
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| Abstract: | 1-Deoxy-D-galactohomonojirimycin was synthesized in seven steps from optically pure allenylstannane 4 and L-lactate-derived aldehyde 5 in 48% overall yield. The key step was the Lewis acid catalyzed reaction of 4 and 5 to give the syn-amino alcohol in excellent yield and very high diastereoselectivity. |
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