Palladium-Catalyzed α-Allylation of Secondary Nitroalkanes with Allylic Alcohols and Strategic Exploitation of Seebach's Reagent for the Total Synthesis of (±)-Adalinine

Chieh Yu Chang, Yen-Ku Wu*

*Corresponding author for this work

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

A method is reported for the catalytic direct coupling of allylic alcohols and nitroalkanes. In the allylation process, the synergistic action of palladium complexes and titanium(IV) alkoxide facilitates the formation of nitronate and π-allylpalladium intermediate. In the cases of reluctant allylations, typically with sterically demanding nitroalkanes, we found the addition of substoichiometric amount of DBU greatly facilitates the desired transformation. We also accomplished a total synthesis of (±)-adalinine through a homoallyl nitroalkane derived from Seebach's reagent.

Original languageEnglish
Pages (from-to)6217-6224
Number of pages8
JournalJournal of Organic Chemistry
Volume83
Issue number11
DOIs
StatePublished - 1 Jun 2018

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