Affiliation:
1. CAS Key Laboratory of Synthetic Chemistry of Natural Substances Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Shanghai 200032 China
2. School of Chemistry and Materials Science Hangzhou Institute for Advanced Study University of Chinese Academy of Sciences Hangzhou 310024 China
Abstract
AbstractChain walking has been an efficient route to realize the functionalization of inert C(sp3)−H bonds, but this strategy is limited to mono‐olefin migration and functionalization. Herein, we demonstrate the feasibility of tandem directed simultaneous migrations of remote olefins and stereoselective allylation for the first time. The adoption of palladium hydride catalysis and secondary amine morpholine as solvent is critical for achieving high substrate compatibility and stereochemical control with this method. The protocol is also applicable to the functionalization of three vicinal C(sp3)−H bonds and thus construct three continuous stereocenters along a propylidene moiety via a short synthetic process. Preliminary mechanistic experiments corroborated the design of simultaneous walking of remote dienes.
Funder
National Natural Science Foundation of China
Science and Technology Innovation Plan Of Shanghai Science and Technology Commission
Natural Science Foundation of Ningbo
Shanghai Rising-Star Program
Cited by
2 articles.
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