Ruthenium-Catalyzed Asymmetric Allylic Alkylation of Isatins

Org Lett. 2020 Apr 3;22(7):2584-2589. doi: 10.1021/acs.orglett.0c00504. Epub 2020 Mar 23.

Abstract

A new ruthenium-based catalytic system for branched-selective asymmetric allylic alkylation is disclosed and applied to the synthesis of chiral isatin derivatives. The catalyst, which is generated in situ from commercially available CpRu(MeCN)3PF6 and a BINOL-derived phosphoramidite, is both highly active (TON up to 180) and insensitive to air and moisture. Additionally, the N-alkylated isatins accessible using this methodology are versatile building blocks that are readily transformed into chiral analogs of achiral drug molecules.

Publication types

  • Research Support, Non-U.S. Gov't