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DOI: 10.1055/s-0036-1591548
Copper-Catalyzed Enantioselective Coupling between Allylboronates and Phosphates Using a Phenol–Carbene Chiral Ligand: Asymmetric Synthesis of Chiral Branched 1,5-Dienes
This work was supported by Grants-in-Aid for Scientific Research (B) (No. 15H03803), JSPS to H.O. and by CREST and ACT-C, JST to M.S.Publication History
Received: 19 December 2017
Accepted after revision: 12 February 2018
Publication Date:
20 March 2018 (online)


Abstract
Details of the Cu-catalyzed enantioselective allyl–allyl coupling reaction between allylboronates and (Z)-allylic phosphates using a new chiral N-heterocyclic carbene (NHC) ligand containing a phenolic hydroxy group are presented. The copper catalysis delivers enantioenriched chiral 1,5-dienes with a tertiary stereogenic center. Compatibility with various functional groups and the use of earth-abundant and relatively low-toxicity copper as a metal are attractive features of this protocol. The utility of the chiral phenol–NHC ligand for enantioselective copper catalysis with organoboron compounds is demonstrated and enantiodiscrimination models are discussed.
Key words
asymmetric catalysis - allylic substitution - synthetic methods copper catalysis - organoboron compoundsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591548.
- Supporting Information