Stereodivergent Synthesis of Tertiary Fluoride-Tethered Allenes via Copper and Palladium Dual Catalysis

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 alpha-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.

Automated summary

The protocol describes the unprecedented stereodivergent synthesis of tertiary fluoride-tethered allenes with a stereogenic center and stereogenic axis via Cu/Pd synergistic catalysis. A wide range of conjugated enynes are coupled with various alpha-fluoroesters in high yields and diastereoselectivity. The novel stereodivergent axial-to-central chirality transfer process enables precise access to the corresponding four stereoisomers of fluorinated hydrofurans.