We report a new protocol for synthesis of L-1-deoxymannojirimycin, L-1-deoxyidonojirimycin, and the N-isopropyl derivative of the latter compound from the readily available precursors (S)-isoserinal hydrate and 2-tert-butyl-2-methyl-1,3-dioxan-5-one. The key steps include diastereoselective proline-catalyzed syn aldol transformation and a reductive amination/cyclization.
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Acids as Proline Co-Catalysts in the Aldol Reaction of 1,3-Dioxan-5-ones. -The stereoselectivity is investigated in the presence of various additives. Py·TosOH and LiCl are found to exert major effects. -(MAJEWSKI*, M.; NIEWCZAS, I.; PALYAM, N.; Synlett 2006, 15, 2387-2390; Dep. Chem., Univ. Saskatchewan, Saskatoon, Sask. S7N 5C9, Can.; Eng.) -Mais 05-150
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