Department of Chemistry, Pohang University of Science and Technology, Hyoja-dong San 31, Pohang, Kyungbuk, Republic of Korea 790-784.
J Am Chem Soc. 2012 Mar 7;134(9):4011-4. doi: 10.1021/ja2116298. Epub 2012 Feb 27.
We developed a conceptually new synthetic strategy which exploits the stereochemical information of labile acyclic N,O-acetals. The key to this strategy, chemo- and stereoselective synthesis of N,O-acetals, was achieved by the Pd-catalyzed addition of sulfonyl-protected homopropargylic amines to alkoxyallene. The N,O-acetals generated in this way were combined with Au-catalyzed cycloisomerization to give an access to 2,6-disubstituted piperidines with stereochemical flexibility.
我们开发了一种全新的合成策略，利用不稳定的无环 N,O-缩醛的立体化学信息。该策略的关键是通过钯催化的磺酰基保护的偕丙胺对烷氧基丙二烯的加成反应，实现了化学选择性和立体选择性的 N,O-缩醛合成。以这种方式生成的 N,O-缩醛与金催化的环异构化反应相结合，为具有立体化学灵活性的 2,6-二取代哌啶提供了一种途径。
