Organocatalytic syn-Aldol Reactions of Dioxanones with (S)-Isoserinal Hydrate: Synthesis of l-Deoxymannojirimycin and l-Deox

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• 作者：Nagarjuna Palyam ; Marek Majewski
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：June 5, 2009
• 年：2009
• 卷：74
• 期：11
• 页码：4390-4392
• 全文大小：146K
• 年卷期：v.74,no.11(June 5, 2009)
• ISSN：1520-6904

文摘

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.