Wang Cong-Shuai, Li Tian-Zhen, Cheng Yu-Chun, Zhou Ji, Mei Guang-Jian, Shi Feng
School of Chemistry and Materials Science , Jiangsu Normal University , Xuzhou , 221116 , China.
J Org Chem. 2019 Mar 15;84(6):3214-3222. doi: 10.1021/acs.joc.8b03004. Epub 2019 Feb 25.
A chiral guanidine-catalyzed asymmetric [4 + 1] cyclization of benzofuran-derived azadienes with 3-chlorooxindoles has been established, which constructed chiral spirooxindole frameworks with in situ generation of a five-membered ring with high diastereoselectivities (up to >95:5 dr) and good enantioselectivities (up to 94:6 er). This reaction represents the first catalytic asymmetric [4 + 1] cyclization of benzofuran-derived azadienes, which will enrich the research field of catalytic asymmetric cyclizations of such reactants. In addition, this reaction provides a useful strategy for the enantioselective construction of five-membered ring-based chiral spirooxindole scaffolds.
已实现手性胍催化苯并呋喃衍生的氮杂二烯与3-氯氧化吲哚的不对称[4 + 1]环化反应，该反应通过原位生成五元环构建了具有高非对映选择性（高达>95:5 dr）和良好对映选择性（高达94:6 er）的手性螺环氧化吲哚骨架。该反应代表了苯并呋喃衍生的氮杂二烯的首例催化不对称[4 + 1]环化反应，将丰富此类反应物的催化不对称环化研究领域。此外，该反应为对映选择性构建基于五元环的手性螺环氧化吲哚支架提供了一种有用的策略。
