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Issue 23, 2018
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Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes

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Abstract

A highly enantioselective Cu-catalyzed borylation of 2-substituted 1,3-dienes is reported. The use of a chiral phosphanamine ligand is essential in achieving high chemo-, regio-, diastereo- and enantioselectivity. It provides access to a variety of homoallylic boronates in consistently high yield and enantiomeric excess with 2-aryl and 2-heteroaryl 1,3-dienes as well as sterically demanding 2-alkyl 1,3-dienes. Preliminary investigations based on a non-linear effect study point to a mechanism involving more than one metal center.

Graphical abstract: Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes

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Publication details

The article was received on 04 Apr 2018, accepted on 22 May 2018 and first published on 23 May 2018


Article type: Edge Article
DOI: 10.1039/C8SC01538D
Citation: Chem. Sci., 2018,9, 5284-5288
  • Open access: Creative Commons BY-NC license
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    Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes

    Y. Liu, D. Fiorito and C. Mazet, Chem. Sci., 2018, 9, 5284
    DOI: 10.1039/C8SC01538D

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