Mei Guang-Jian, Li Dan, Zhou Gui-Xiang, Shi Qian, Cao Zheng, Shi Feng
School of Chemistry and Material Science, Jiangsu Normal University, Xuzhou, 221116, China.
Chem Commun (Camb). 2017 Sep 5;53(72):10030-10033. doi: 10.1039/c7cc05595a.
A catalytic asymmetric decarboxylative [4+2] cycloaddition of vinyl benzoxazinanones with methyleneindolinones has been established, which provided a series of chiral tetrahydroquinoline-based 3,3'-spirooxindoles in high yields (up to 96%) and with excellent diastereo- and enantioselectivities (all >95 : 5 d.r., up to 99% ee). This reaction not only represents the first example of catalytic enantioselective [4+2] cycloaddition between methyleneindolinones and Pd-containing 1,4-dipoles, but also demonstrates the great practicability of catalytic asymmetric decarboxylative cycloadditions in the synthesis of enantio-enriched polycyclic compounds.
已实现乙烯基苯并恶嗪酮与亚甲基吲哚酮的催化不对称脱羧[4+2]环加成反应，该反应以高收率（高达96%）提供了一系列基于手性四氢喹啉的3,3'-螺环氧化吲哚，且具有优异的非对映和对映选择性（所有非对映体比例>95:5，对映体过量高达99%）。该反应不仅代表了亚甲基吲哚酮与含钯1,4-偶极子之间催化对映选择性[4+2]环加成的首例，还证明了催化不对称脱羧环加成在对映体富集多环化合物合成中的巨大实用性。
