Efficient and Easy Access to Optically Pure Tetrasubstituted Tetra­hydrofurans via Stereoselective Opening of C2-Symmetric Epoxide and Aziridine Rings

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• 作者：Venkata Pavan Kumar Kondapi ; Olivier-Mohamad Soueidan ; Seyedeh Nargess Hosseini ; Nauras Jabari and Frederick G. West
• 关键词：Oxygen heterocycles ; Nitrogen heterocycles ; Carbohydrates ; Small-ring systems ; Ring opening ; Michael addition
• 刊名：European Journal of Organic Chemistry
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：2016
• 期：7
• 页码：1367-1379
• 全文大小：4051K
• ISSN：1099-0690

文摘

An efficient and facile protocol to functionalize position C-3 of 2,5-anhydro-D-mannitol via diastereoselective ring opening of a C₂-symmetric epoxide 2,5:3,4-dianhydro-D-allitol 3 has been developed. This method is protecting-group-free, high-yielding, and provides access to C-3-modified 2,5-anhydro-D-mannitols 5a, 11a–15a and 16–17. This method was then extrapolated to the synthesis of a C₂-symmetric aziridine, which underwent ring opening with various nucleophiles to provide access to C-3- and C-4-modified 2,5-anhydro-D-mannitols 19–27 in excellent global yields and moderate to good diastereoselectivities. These structures and their derivatives are potentially useful in a variety of applications, including organocatalysis of asymmetric Michael additions as demonstrated with diamine monosulfonamides 28a and 28b, which provide adducts with complementary enantioselectivity.