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Synfacts 2011(11): 1229-1229  
DOI: 10.1055/s-0031-1289199
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral C(sp³) Boronate Building Blocks

Contributor(s): Paul Knochel, Thomas Kunz
J. Li, M. D. Burke*
University of Illinois at Urbana-Champaign, USA
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

Herein, the stereoselective synthesis of a wide range of oxiranyl C(sp³) boronates from the corresponding olefins based on a pinene-derived iminodiacetic acid ligand is reported. These building blocks can be transformed into α-boryl aldehydes and onwards to B-protected haloboronic acids, which represent a new type of nucleophilic/electrophilic bifunctional reagent.