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Iron‐Catalyzed Cross‐Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols
Author(s) -
Posevins Daniels,
BermejoLópez Aitor,
Bäckvall JanE.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202106742
Subject(s) - propargyl , reagent , chemistry , stereospecificity , catalysis , combinatorial chemistry , grignard reaction , coupling reaction , chirality (physics) , organic chemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
Herein we disclose an iron‐catalyzed cross‐coupling reaction of propargyl ethers with Grignard reagents. The reaction was demonstrated to be stereospecific and allows for a facile preparation of optically active allenes via efficient chirality transfer. Various tri‐ and tetrasubstituted fluoroalkyl allenes can be obtained in good to excellent yields. In addition, an iron‐catalyzed cross‐coupling of Grignard reagents with α‐alkynyl oxetanes and tetrahydrofurans is disclosed herein, which constitutes a straightforward approach towards fully substituted β‐ or γ‐allenols, respectively.