Department of Chemistry, POSTECH (Pohang University of Science and Technology), Hyoja-dong San 31, Pohang, Kyungbuk, Republic of Korea 790-784.
J Am Chem Soc. 2009 Oct 21;131(41):14660-1. doi: 10.1021/ja906744r.
A new gold(I)-catalyzed cycloisomerization to access highly substituted piperidines has been developed. By combining a conceptually new way of generating iminium ions using cationic gold(I) complexes and an efficient cyclization reaction that can minimize a potentially competing aza-Cope rearrangement, the proposed reaction successfully circumvents a long-standing problem in the classical aza-Prins reaction. Synthetic utility of the catalytic reaction was demonstrated by a synthesis of optically active 2-alkyl-piperidin-4-one.
一种新的金（I）催化的环化异构化反应已经被开发出来，用于构建高度取代的哌啶。通过结合使用阳离子金（I）配合物生成亚胺离子的新概念方法，以及一种有效的环化反应，可以最小化潜在的竞争氮杂-Cope 重排，所提出的反应成功地规避了经典氮杂-Prins 反应中的一个长期存在的问题。通过合成光学活性的 2-烷基-哌啶-4-酮，展示了催化反应的合成实用性。
