Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration

Tri- and tetrasubstituted allenylboronic acids were prepared a new versatile copper-catalyzed methodology. The densely functionalized allenylboronic acids readily undergo propargylboration reactions with ketones and imines without any additives. Catalytic asymmetric propargylborylation of ketones is...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2018, Vol.9 (13), p.3305-3312
Main Authors: Zhao, Jian, Jonker, Sybrand J T, Meyer, Denise N, Schulz, Göran, Tran, C Duc, Eriksson, Lars, Szabó, Kálmán J
Format: Article
Language:English
Subjects:
Acids
Additives
Alcohol
Alcohols
Alkynes
Amines
Catalysis
Chemical reactions
Chemical synthesis
Chemistry
Copper
Imines
Ketones
Stereoselectivity
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Summary:Tri- and tetrasubstituted allenylboronic acids were prepared a new versatile copper-catalyzed methodology. The densely functionalized allenylboronic acids readily undergo propargylboration reactions with ketones and imines without any additives. Catalytic asymmetric propargylborylation of ketones is demonstrated with high stereoselectivity allowing for the synthesis of highly enantioenriched tertiary homopropargyl alcohols. The reaction is suitable for kinetic resolution of racemic allenylboronic acids affording alkynes with adjacent quaternary stereocenters.
ISSN:2041-6520
2041-6539
2041-6539
DOI:10.1039/c7sc05123a