Access to chiral homoallylic vicinal diols from carbonyl allylation of aldehydes with allyl ethers via palladium-catalyzed allylic C-H borylation

Chiral homoallylic vicinal diols are found in many bioactive compounds and are among the most versatile functional groups in organic chemistry. Here, we describe an asymmetric carbonyl allylation of aldehydes with allyl ethers proceeding via allylic C-H borylation enabled by palladium and chiral phosphoric acid sequential catalysis, providing facile access to homoallylic vicinal anti-diols in high yields and with excellent stereoselectivity. This protocol enables the total synthesis of aigialomycin D to be finished within 7 steps.

Automated summary

The method involves asymmetric carbonyl allylation of aldehydes via allylic C-H borylation enabled by palladium and chiral phosphoric acid sequential catalysis, providing homoallylic vicinal anti-diols in high yields and excellent stereoselectivity. This protocol allows the total synthesis of aigialomycin D to be completed within 7 steps.