Transition-Metal-Free Synthesis of Enantioenriched Tertiary and Quaternary α-Chiral Allylsilanes

Access to enantioenriched tertiary and quaternary α-chiral allysilanes without any transition-metal catalyst is reported. This was achieved by enantioselective allylic displacement of γ-silylated allylic bromides through Lewis base activation of Grignard reagents by a bidentate chiral NHC ligand. Th...

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Bibliographic Details
Published inChemistry : a European journal Vol. 29; no. 59; p. e202302227
Main Authors Sevillano, Rubén Pérez, Ferreira, Franck, Jackowski, Olivier
Format Journal Article
LanguageEnglish
Published Germany Wiley Subscription Services, Inc 23.10.2023
Wiley-VCH Verlag
Subjects
Bromides
Catalysts
Chemical Sciences
Chemistry
Enantiomers
Lewis base
Reagents
Substrates
enantioselectivity
Grignard reagents
allylsilanes
allylic substitution
N-heterocyclic carbenes
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Summary:Access to enantioenriched tertiary and quaternary α-chiral allysilanes without any transition-metal catalyst is reported. This was achieved by enantioselective allylic displacement of γ-silylated allylic bromides through Lewis base activation of Grignard reagents by a bidentate chiral NHC ligand. The process afforded both high γ-regio- and enantioselectivity and is compatible with a wide range of silyl groups on the substrates.
Bibliography:ObjectType-Article-1
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ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202302227