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Synlett 2023; 34(20): 2491-2495
DOI: 10.1055/a-2108-9720
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Special Issue Dedicated to Prof. Hisashi Yamamoto

Iridium-Catalyzed Asymmetric Allylation of Indoles via Kinetic Resolution of 1-Alken-4-yn-3-ols

Takahiro Sawano 
a   Department of Chemistry and Biological Science, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan
,
Yuki Yasumura
a   Department of Chemistry and Biological Science, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan
,
Kyohei Kuwabara
a   Department of Chemistry and Biological Science, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan
,
Hikaru Sugiura
a   Department of Chemistry and Biological Science, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan
,
Kana Takahashi
a   Department of Chemistry and Biological Science, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan
,
Eri Ishikawa
b   Department of Applied Chemistry, Chubu University, 1200 Matsumoto-cho, Kasugai 487-8501, Japan
,
Ryo Takeuchi∗
a   Department of Chemistry and Biological Science, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan
› Author AffiliationsThis work was supported by Aoyama Gakuin University Research Institute grant program for promotion of SDGs-related research and a grant from Aoyama Gakuin Research Institute.
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Dedicated to Prof. Hisashi Yamamoto on the occasion of his 80th birthday

Abstract

We report the iridium-catalyzed asymmetric allylation of indoles via kinetic resolution of 1-alken-4-yn-3-ols to form chiral 1-alken-4-yn-3-ols and branched allylated products with high selectivity. 1-Alken-4,6-diyn-3-ol was also found to be suitable for this asymmetric allylation and gave the products in high yield and enantioselectivity. Other nucleophiles such as a malonic ester and a thiol, besides indoles, reacted to give allylated products and 1-alken-4-yn-3-ols with high enantioselectivities.

Key words

iridium - asymmetric catalysis - allylation - 1-alken-4-yn-3-ols - indoles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2108-9720.
  • Supporting Information


Publication History

Received: 30 April 2023

Accepted after revision: 12 June 2023

Accepted Manuscript online:
12 June 2023

Article published online:
17 July 2023

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  • References and Notes

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