Synthesis of chiral allylic phosphonates via asymmetric reductive cross-coupling of a-bromophosphonates and vinyl bromides

Chiral phosphine-containing skeletons play a pivotal role in bioactive natural products, pharmaceuticals, chiral catalysts, and ligands. Despite considerable progress has been made in the synthesis of chiral phosphorus compounds, the development of facile and modular methods to access chiral allylic phosphorus compounds remains challenging due to the simultaneous control required for reactivity, enantioselectivity, and stereoselectivity. Herein, we present a general and modular platform to achieve the asymmetric reductive cross-coupling of a-bromophosphonates and vinyl bromides, enabling the synthesis of highly valuable chiral allylic phosphonate products with remarkable yields, enantioselectivities, and stereoselectivities.

Automated summary

Chiral phosphine-containing skeletons are crucial in various applications including bioactive natural products, pharmaceuticals, chiral catalysts, and ligands. However, the development of convenient and modular methods for accessing chiral allylic phosphorus compounds has remained challenging due to the simultaneous control required for reactivity, enantioselectivity, and stereoselectivity. In this study, a general and modular platform for asymmetric reductive cross-coupling of a-bromophosphonates and vinyl bromides is presented, enabling the synthesis of highly valuable chiral allylic phosphonate products with remarkable yields, enantioselectivities, and stereoselectivities.