Xie Ruyu, Li Rui, Zhao Qingzheng, Zhao Yongxing, Yao Jinzhong, Miao Maozhong
School of Chemistry and Chemical Engineering, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, P. R. China.
College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, P. R. China.
J Org Chem. 2023 Apr 7;88(7):4778-4789. doi: 10.1021/acs.joc.2c02805. Epub 2023 Mar 20.
The metal-free cyclization of allenyl ketones and -toluenesulfonylmethyl isocyanide (TosMIC), promoted by CsCO, provides a convenient access to tetrasubstituted pyrroles in which an acyl group undergoes 1,2-migration. This tandem Michael addition/annulative migration synthetic strategy is general and high-yielding for various substituted allenyl ketones. Moreover, a phosphoryl or ester moiety is also a suitable functionality to enable such migration.
在碳酸铯促进下，烯丙基酮与对甲苯磺酰甲基异腈（TosMIC）进行无金属环化反应，可方便地合成四取代吡咯，其中酰基会发生1,2-迁移。这种串联迈克尔加成/环化迁移的合成策略对于各种取代的烯丙基酮来说具有通用性且产率很高。此外，磷酰基或酯基部分也是能够实现这种迁移的合适官能团。
