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Issue 6, 2017
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Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki–Miyaura cross-coupling

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Abstract

The rhodium-catalyzed, directed catalytic asymmetric hydroboration of γ,δ-unsaturated amides affords a direct route to chiral acyclic secondary γ-borylated carbonyl derivatives in high enantiomeric purity. In contrast to a similar β-borylated amide derivative, the γ-borylated amide undergoes Suzuki–Miyaura cross-coupling with stereoretention. The utility of the boronic ester products is further illustrated by other stereospecific C–B bond transformations leading to γ-amino acid derivatives, 1,4-amino alcohols, and 5-substituted-γ-lactone and γ-lactam ring systems.

Graphical abstract: Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki–Miyaura cross-coupling

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Publication details

The article was received on 09 Mar 2017, accepted on 19 Apr 2017 and first published on 24 Apr 2017


Article type: Edge Article
DOI: 10.1039/C7SC01093A
Citation: Chem. Sci., 2017,8, 4511-4516
  • Open access: Creative Commons BY-NC license
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    Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki–Miyaura cross-coupling

    G. L. Hoang and J. M. Takacs, Chem. Sci., 2017, 8, 4511
    DOI: 10.1039/C7SC01093A

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