posted on 2023-12-28, 14:34authored byBo Jiang, Hao-Tian Wang, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Although the asymmetric hydroalkoxylation of 1,3-dienes
has been
achieved recently, the development of a modular and mechanistically
distinct strategy for concurrently introducing an alkoxyl group and
another chiral moiety into 1,3-dienes remains to be disclosed. Presented
herein is a palladium(0)-π-Lewis base-catalyzed asymmetric hydroxymethylative
etherification reaction of 1,3-dienes, isatins, and aliphatic alcohols,
proceeding through a cascade vinylogous addition and allylic etherification
sequence. This three-component reaction exhibits a broad substrate
scope and good functionality tolerance under mild catalytic conditions,
generally furnishing structurally diverse chiral 1,3-diol derivatives
bearing two stereogenic centers with moderate-to-high levels of diastereo-
and enantioselectivity, which can be further converted to valuable
frameworks with higher molecular complexity. In addition, a few control
experiments were conducted to elucidate the reaction process.