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author:

Ma, Xingxing (Ma, Xingxing.) [1] | Tan, Mengwei (Tan, Mengwei.) [2] | Li, Luo (Li, Luo.) [3] | Zhong, Zihao (Zhong, Zihao.) [4] | Li, Puhui (Li, Puhui.) [5] | Liang, Jinchao (Liang, Jinchao.) [6] | Song, Qiuling (Song, Qiuling.) [7] (Scholars:宋秋玲)

Indexed by:

Scopus SCIE

Abstract:

Asymmetric synthesis based on a metallate shift of tetracoordinate borons is an intriguing and challenging topic. Despite the construction of central chirality from tetracoordinate boron species via a 1,2-metallate shift, catalytic asymmetric synthesis of axially chiral compounds from such boron 'ate' complexes is an ongoing challenge. Axially chiral alkenes have received great attention due to their unique characteristics and intriguing molecular scaffolds. Here we report an enantioselective nickel-catalysed strategy for the construction of axially chiral alkenes via a 1,3-metallate shift of alkynyl tetracoordinate boron species. The chemoselectivity, regioselectivity and atroposelectivity can be regulated and well-controlled from readily accessible starting materials with a cheap transition-metal catalyst. Downstream transformations indicate the powerful conversion ability of such compounds in this protocol, and late-stage elaborations of bioactive compounds can also be achieved. Mechanistic experiments reveal that regioselective syn-addition of an aryl-Ni complex with a carbon-carbon triple bond and subsequent 1,3-phenyl migration are the two key steps for the synthesis of axially chiral alkenes. Enantioselective transformations based on tetracoordinate borons are elusive. Now, an enantioselective nickel-catalysed strategy for the construction of axially chiral alkenes has been reported, via a 1,3-metallate shift of alkynyl tetracoordinate boron species. The reaction uses readily accessible starting materials and a cheap transition-metal catalyst, and the chemoselectivity, regioselectivity and atroposelectivity could be well controlled.

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Community:

  • [ 1 ] [Ma, Xingxing]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou, Fujian, Peoples R China
  • [ 2 ] [Tan, Mengwei]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou, Fujian, Peoples R China
  • [ 3 ] [Li, Luo]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou, Fujian, Peoples R China
  • [ 4 ] [Zhong, Zihao]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou, Fujian, Peoples R China
  • [ 5 ] [Li, Puhui]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou, Fujian, Peoples R China
  • [ 6 ] [Liang, Jinchao]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou, Fujian, Peoples R China
  • [ 7 ] [Song, Qiuling]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou, Fujian, Peoples R China

Reprint 's Address:

  • 宋秋玲

    [Song, Qiuling]Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou, Fujian, Peoples R China

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Source :

NATURE CHEMISTRY

ISSN: 1755-4330

Year: 2024

Issue: 1

Volume: 16

1 9 . 2 0 0

JCR@2023

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count: 25

ESI Highly Cited Papers on the List: 3 Unfold All

  • 2024-11
  • 2024-9
  • 2024-7

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 0

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