Wang Ruo-Wen, Qing Feng-Ling
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Org Lett. 2005 May 26;7(11):2189-92. doi: 10.1021/ol050558h.
[reaction: see text]. D-1,4,6-trideoxy-4,4-difluoronojirimycin and L-1,4,6-trideoxy-4,4-difluoronojirimycin, a novel series of gem-4,4-difluoromethylenated azasugars, were synthesized from CF3CH2OH in 10 steps. A key step was the highly diastereoselective construction of the piperidine ring via reductive amination.
[反应：见正文]。D - 1,4,6 - 三脱氧 - 4,4 - 二氟野尻霉素和L - 1,4,6 - 三脱氧 - 4,4 - 二氟野尻霉素是一系列新型的偕 - 4,4 - 二氟亚甲基化氮杂糖，由三氟乙醇经10步反应合成。关键步骤是通过还原胺化反应进行哌啶环的高非对映选择性构建。
