4.8 Article

Copper-Catalyzed γ-Selective Allyl-Alkyl Coupling between Allylic Phosphates and Alkylboranes

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 9, Pages 2895-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja9109105

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Funding

  1. Grants-in-Aid for Scientific Research (B) [21350020]
  2. Young Scientists (B) [21750086]
  3. JSPS
  4. Grants-in-Aid for Scientific Research [21350020, 21750086] Funding Source: KAKEN

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Copper-catalyzed allyl-alkyl coupling between allylic phosphates and alkylboranes, prepared by hydroboration of alkenes with 9-BBN-H, takes place with complete gamma- and E-selectivities and with preferential 1,3-anti stereochemistry. The reaction tolerates various functional groups in both the allylic phosphate and alkylborane. Catalytic mechanisms involving transmetalation between a trialkyl(alkoxo)borate and a copper(I) complex to form an alkylcopper(I) species are proposed.

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