Axially chiral <i>N</i>-alkyl-<i>N</i>-cinnamoyl amide type P,olefin ligands for Pd-catalyzed reactions-Reference-Cited by-同舟云学术

Axially chiral N-alkyl-N-cinnamoyl amide type P,olefin ligands for Pd-catalyzed reactions

Published:2023 Issue:13 Volume:21 Page:2775-2778
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Mino Takashi¹²³^ORCID,Takaya Kaho¹,Koki Kaito¹,Akimoto Natsume¹,Yoshida Yasushi¹²³^ORCID,Kasashima Yoshio⁴,Sakamoto Masami¹²^ORCID

Affiliation:

1. Graduate School of Engineering, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

2. Molecular Chirality Research Center, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

3. Soft Molecular Activation Research Center, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

4. Education Center, Chiba Institute of Technology, Shibazono 2-2-1, Narashino, Chiba 275-0023, Japan

Abstract

We synthesized cinnamoyl amide type compounds 1 with axial chirality. We demonstrated the use of (–)-1 for chiral ligands in Pd-catalyzed asymmetric allylic substitution reactions of allylic esters with indoles (up to 97% ee).

Funder

Japan Society for the Promotion of Science

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/OB/D3OB00224A

Reference19 articles.

1. Development of a novel phosphoramidite-selenide ligand for Pd-catalyzed asymmetric allylic substitution

2. Phosphoric acid-catalyzed atroposelective construction of axially chiral arylpyrroles

3. Spiro Indane-Based Phosphine-Oxazolines as Highly Efficient P,N Ligands for Enantioselective Pd-Catalyzed Allylic Alkylation of Indoles and Allylic Etherification

4. Rational Design and Synthesis of [5]Helicene-Derived Phosphine Ligands and Their Application in Pd-Catalyzed Asymmetric Reactions

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1. Synthesis of Branch-Type 3-Allylindoles from N-Alkyl-N-cinnamyl-2-ethynylaniline Derivatives Using π–Allylpalladium Chloride Complex as a Catalyst;The Journal of Organic Chemistry;2024-05-10

2. Palladium‐Catalyzed Enantioselective Indole Allylic Alkylation with Chiral Phosphoramidite‐Selenide‐Based Ligands;European Journal of Organic Chemistry;2023-12-06