Umpolung Reaction of alpha-Imino Thioesters and the Subsequent C-C Bond Formation with the Unexpected Alkylthio Rearrangement

作者：Mizota Isao^*; Ueda Chihiro; Tesong Yun; Tsujimoto Yusuke; Shimizu Makoto^*

来源：Organic Letters, 2018, 20(8): 2291-2296.

DOI：10.1021/acs.orglett.8b00639

An umpolung reaction of the alpha-imino thioester was examined, and we found that alpha-imino thioesters were more effective substrates for the umpolung N-alkylation than conventional alpha-imino esters and they gave N-alkylated amino thioesters in high yields under mild reaction conditions in a short time. A new type of C-C bond formation followed by an unexpected rearrangement of the alkylthio group took place with the unsaturated ketones to afford the beta-alkylthio-alpha-amino thioesters in high yields with good diastereoselectivity.

• 出版日期2018-4-20