Wang Yu-Jiao, Zhao Li-Ming
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, China.
Chemistry. 2023 Dec 19;29(71):e202302111. doi: 10.1002/chem.202302111. Epub 2023 Oct 31.
Azecine fragments are frequently presented in natural products and bioactive compounds. However, minor efforts have been devoted to these 10-membered N-heterocycles, and their synthesis is still challenging. Reported herein is the first catalytic formal [6+4] cycloaddition for the synthesis of 10-membered azecines. Under palladium catalysis, the reaction of δ-vinylvalerolactones and benzofuran-derived azadienes proceeds smoothly to afford benzofuran-fused azecines with high diastereoselectivity in moderate to good yields. A unique transannular reaction of these 10-membered azecines for the construction of polycyclic compounds is also demonstrated.
氮杂环辛因片段经常存在于天然产物和生物活性化合物中。然而，针对这些十元氮杂环的研究较少，其合成仍然具有挑战性。本文报道了首例用于合成十元氮杂环辛因的催化形式[6+4]环加成反应。在钯催化下，δ-乙烯基戊内酯与苯并呋喃衍生的氮杂二烯顺利反应，以中等至良好的产率、高非对映选择性得到苯并呋喃稠合的氮杂环辛因。还展示了这些十元氮杂环辛因用于构建多环化合物的独特跨环反应。
