CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.
J Am Chem Soc. 2021 May 19;143(19):7285-7291. doi: 10.1021/jacs.1c03157. Epub 2021 May 10.
Herein we describe a protocol for the unprecedented stereodivergent synthesis of tertiary fluoride-tethered allenes bearing a stereogenic center and stereogenic axis via Cu/Pd synergistic catalysis. A broad scope of conjugated enynes are coupled with various α-fluoroesters in high yields with high diastereoselectivities and generally >99% ee. In addition, the four stereoisomers of the allene products ensure precise access to the corresponding four stereoisomers of the fluorinated hydrofurans via a novel stereodivergent axial-to-central chirality transfer process.
在这里，我们描述了一种通过铜/钯协同催化，从前所未有的立体发散方式合成带有手性中心和手性轴的三氟化物键联丙二烯的方案。各种共轭烯炔与各种α-氟酯以高收率和高非对映选择性（通常大于 99%ee）进行偶联。此外，丙二烯产物的四个立体异构体确保了通过新颖的立体发散轴向-中心手性转移过程，精确获得相应的四个氟代四氢呋喃的立体异构体。
