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Catalytic Use of Zinc Amide for Transmetalation with Allylboronates: General and Efficient Catalytic Allylation of Carbonyl Compounds, Imines, and Hydrazones

The efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron‐to‐zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proc... Full description

Journal Title: Advanced Synthesis & Catalysis 15 April 2013, Vol.355(6), pp.1193-1205
Main Author: Cui, Yi
Other Authors: Li, Wei , Sato, Takehiro , Yamashita, Yasuhiro , Kobayashi, Shū
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1615-4150 ; E-ISSN: 1615-4169 ; DOI: 10.1002/adsc.201201134
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recordid: wj10.1002/adsc.201201134
title: Catalytic Use of Zinc Amide for Transmetalation with Allylboronates: General and Efficient Catalytic Allylation of Carbonyl Compounds, Imines, and Hydrazones
format: Article
creator:
  • Cui, Yi
  • Li, Wei
  • Sato, Takehiro
  • Yamashita, Yasuhiro
  • Kobayashi, Shū
subjects:
  • Allylation
  • Catalysts
  • Metal Amides
  • Transmetalation
  • Zinc
ispartof: Advanced Synthesis & Catalysis, 15 April 2013, Vol.355(6), pp.1193-1205
description: The efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron‐to‐zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (∼0.1 mol%). A mechanistic study revealed that transmetalation was a rate‐determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral diamine ligands.
language: eng
source:
identifier: ISSN: 1615-4150 ; E-ISSN: 1615-4169 ; DOI: 10.1002/adsc.201201134
fulltext: fulltext
issn:
  • 1615-4150
  • 16154150
  • 1615-4169
  • 16154169
url: Link


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titleCatalytic Use of Zinc Amide for Transmetalation with Allylboronates: General and Efficient Catalytic Allylation of Carbonyl Compounds, Imines, and Hydrazones
creatorCui, Yi ; Li, Wei ; Sato, Takehiro ; Yamashita, Yasuhiro ; Kobayashi, Shū
ispartofAdvanced Synthesis & Catalysis, 15 April 2013, Vol.355(6), pp.1193-1205
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subjectAllylation ; Catalysts ; Metal Amides ; Transmetalation ; Zinc
descriptionThe efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron‐to‐zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (∼0.1 mol%). A mechanistic study revealed that transmetalation was a rate‐determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral diamine ligands.
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titleCatalytic Use of Zinc Amide for Transmetalation with Allylboronates: General and Efficient Catalytic Allylation of Carbonyl Compounds, Imines, and Hydrazones
descriptionThe efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron‐to‐zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (∼0.1 mol%). A mechanistic study revealed that transmetalation was a rate‐determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral diamine ligands.
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titleCatalytic Use of Zinc Amide for Transmetalation with Allylboronates: General and Efficient Catalytic Allylation of Carbonyl Compounds, Imines, and Hydrazones
authorCui, Yi ; Li, Wei ; Sato, Takehiro ; Yamashita, Yasuhiro ; Kobayashi, Shū
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abstractThe efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron‐to‐zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (∼0.1 mol%). A mechanistic study revealed that transmetalation was a rate‐determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral diamine ligands.
copWeinheim
pubWILEY‐VCH Verlag
doi10.1002/adsc.201201134
pages1193-1205
date2013-04-15