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Synthesis 2021; 53(19): 3564-3572
DOI: 10.1055/a-1493-6420
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Iron-Catalyzed Stereoselective Allylboration of 3,4-Dihydroisoquinolines with Potassium Allyltrifluoroborates

Yong Fang‡
a   Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Rd., Hefei, 230009, P. R. of China
,
Xiaoling Hu‡
a   Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Rd., Hefei, 230009, P. R. of China
,
Zhuangzhuang Shi
a   Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Rd., Hefei, 230009, P. R. of China
,
Xu Zhao
a   Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Rd., Hefei, 230009, P. R. of China
,
Raveendra Reddy Gopireddy
a   Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Rd., Hefei, 230009, P. R. of China
b   School of Material Science and Engineering, Hefei University of Technology, 193 Tunxi Rd., Hefei, 230009, P. R. of China
,
Yunfei Luo  ∗
a   Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Rd., Hefei, 230009, P. R. of China
› Author AffiliationsThe authors thank the financial support from Hefei University of Technology and Fundamental Research Funds for the Central Universities.
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Abstract

An iron-catalyzed allyation of isoquinoline with potassium allyltrifluoroborate is described. The operation of this reaction is very simple and highly practical. The diastereoisomer having two adjacent chiral centers were obtained in single anti-configuration.

Key words

iron catalysis - potassium allyltrifluoroborate - allylboration - tetrahydroquinoline

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1493-6420. Included are NMR spectra and the crystal structures of compounds 3lc and 3ld.
  • Supporting Information

Primary Data



Publication History

Received: 14 March 2021

Accepted after revision: 28 April 2021

Accepted Manuscript online:
28 April 2021

Article published online:
25 May 2021

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