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

ABSTRACT: Tri- and tetrasubstituted allenylboronic acids were prepared via 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.

SUBMITTER: Zhao J

PROVIDER: S-EPMC5915797 | biostudies-other | 2018 Apr

REPOSITORIES: biostudies-other

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

Zhao Jian J Jonker Sybrand J T SJT Meyer Denise N DN Schulz Göran G Tran C Duc CD Eriksson Lars L Szabó Kálmán J KJ

Chemical science 20180219 13

Tri- and tetrasubstituted allenylboronic acids were prepared <i>via</i> 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 al ...[more]

PMID: 29732108

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