Enantioselective Synthesis of α-Chiral Propargylic Silanes by Copper-Catalyzed 1,4-Selective Addition of Silicon Nucleophiles to Enyne-Type α,β,γ,δ-Unsaturated Acceptors
Wenbin Mao and Martin Oestreich*
*Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany,
Email: martin.oestreich
tu-berlin.de
W. Mao, M. Oestreich, Org. Lett., 2020, 22, 8096-8100.
DOI: 10.1021/acs.orglett.0c03046
see article for more reactions
Abstract
A copper-catalyzed deconjugative addition of silicon nucleophiles to a broad range of enyne-type α,β,γ,δ-unsaturated acceptors provides α-chiral propargylic silanes with excellent enantiomeric excesses. The method is 1,4-selective with hardly any formation of the 1,6-adduct. The double-bond geometry is shown to be critical for achieving this chemoselectivity.
see article for more examples
(R,R)-QuinoxP*
Key Words
ID: J54-Y2020
