ol8b02655_si_001.pdf (14.19 MB)
Iridium-Catalyzed Enantioselective and Diastereoselective Allylation of Dioxindoles: A One-Step Synthesis of 3‑Allyl-3-hydroxyoxindoles
journal contribution
posted on 2018-09-21, 18:03 authored by Rui He, Shanchao Wu, Haoming Tang, Xiaohong Huo, Zhenliang Sun, Wanbin ZhangAn iridium-catalyzed asymmetric allylation
of dioxindoles, 3-hydroxyoxindoles,
regulated by prosthetic groups has been accomplished under mild conditions.
The methodology is applicable to a diverse array of 3-hydroxyoxindole
and cinnamyl acetate substrates. A range of 3-allyl-3-hydroxyoxindoles
containing vicinal tetrasubstituted and trisubstituted stereocenters
can be efficiently synthesized in one-step with excellent enantioselectivity
(up to >99% enaniomeric excess (ee)) and good diastereoselectivity
(up to 11:1 diastereomeric ratio (dr)).