Li Yong, Ye Zhishi, Bellman Tabitha M, Chi Teng, Dai Mingji
†Department of Chemistry and Center for Cancer Research, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.
‡Department of Chemistry, Tsinghua University, Beijing 100084, China.
Org Lett. 2015 May 1;17(9):2186-9. doi: 10.1021/acs.orglett.5b00782. Epub 2015 Apr 17.
The first copper-catalyzed ring-opening electrophilic trifluoromethylation and trifluoromethylthiolation of cyclopropanols to form Csp3-CF3 and Csp3-SCF3 bonds have been realized. These transformations are efficient for the synthesis of β-CF3- and β-SCF3-substituted carbonyl compounds that are otherwise challenging to access. The reaction conditions are mild and tolerate a wide range of functional groups. Application to a concise synthesis of LY2409021, a glucagon receptor antagonist that is used in clinical trials for type 2 diabetes mellitus, is reported as well.
首次实现了铜催化环丙醇的开环亲电三氟甲基化和三氟甲硫基化反应,以形成Csp3-CF3和Csp3-SCF3键。这些转化对于合成β-CF3-和β-SCF3-取代的羰基化合物非常有效,而这些化合物用其他方法很难合成。反应条件温和,能兼容多种官能团。本文还报道了该反应在简洁合成LY2409021中的应用,LY2409021是一种胰高血糖素受体拮抗剂,正在用于2型糖尿病的临床试验。