Shi Yinrui, Chen Lirong, Gao Qi, Li Jiuling, Guo Yafei, Fan Baomin
Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming 650500, China.
School of Chemistry & Environment, Key Laboratory of Advanced Synthetic Chemistry (Yunnan Minzu University) State Ethnic Affairs Commission, Yunnan Minzu University, Kunming 650500, China.
Org Lett. 2023 Sep 8;25(35):6495-6500. doi: 10.1021/acs.orglett.3c02138. Epub 2023 Aug 30.
Here, we report the first catalytic enantioselective 1,4-addition of diarylphosphine oxides to α,β-unsaturated thioesters. Importantly, the most common and commercial oxazaborolidine (CBS) was employed as a catalyst for its new application without being activated by strong protonic acids or Lewis acids and led to the chiral thioesters in excellent yields and enantioselectivities. Furthermore, this method features mild reaction conditions (room temperature and air-insensitive), good substrate tolerance, and easy scalability.
