4.5 Article

Iridium Catalysed Asymmetric Allylic Substitution Reaction of Indolizine Derivatives

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 6, Pages 1500-1507

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100171

Keywords

Iridium catalysis; Indolizine; Allylic substitution; Asymmetric synthesis

Funding

  1. National Natural Science Foundation of China [21672048]
  2. Natural Science Foundation of Zhejiang Province [LY18B020015]
  3. Hangzhou Science and Technology Development Plan Project [20191203B15]
  4. Hangzhou City

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The highly efficient direct asymmetric allylic substitution (AAS) reaction of indolizine derivatives with allylic alcohols was achieved by combining a chiral iridium complex catalyst with Lewis acid under mild conditions, delivering enantioenriched products in high yields and excellent selectivities. This protocol stands out for its availability of starting materials, mild conditions, broad substrate scope, high yields, excellent selectivity, and easy scalability, providing an efficient approach for the synthesis of chiral indolizines.
A highly efficient direct asymmetric allylic substitution (AAS) reaction of indolizine derivatives with allylic alcohols for accessing enantioenriched indolizine derivatives was realized by combining a chiral iridium complex catalyst with Lewis acid under mild reaction conditions, delivering various chiral allylation products in remarkably high yields and excellent enantioselectivities. This protocol distinguishes itself by availability of the starting materials, mild reaction conditions, broad substrate scope, high yields, excellent selectivity and easy scale-up in a stereoselective manner, which provides a highly efficient protocol for chiral indolizines.

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