Issue 31, 2016
From the journal:

Organic & Biomolecular Chemistry

Chiral N-1-adamantyl-N-trans-cinnamylaniline type ligands: synthesis and application to palladium-catalyzed asymmetric allylic alkylation of indoles†

Takashi Mino,*ab   Kenji Nishikawa,a   Moeko Asano,a   Yamato Shima,a   Toshibumi Ebisawa,a   Yasushi Yoshidaab  and  Masami Sakamotoab  

* Corresponding authors

a Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
E-mail: tmino@faculty.chiba-u.jp

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

Abstract

Such chiral phosphine–internal olefin hybrid type ligands as N-1-adamantyl-N-cinnamylaniline derivatives 1 with C(aryl)–N(amine) bond axial chirality were synthesized and utilized for the palladium-catalyzed asymmetric allylic alkylation of indoles to afford the desired products in high enantioselectivities (up to 98% ee).

Graphical abstract: Chiral N-1-adamantyl-N-trans-cinnamylaniline type ligands: synthesis and application to palladium-catalyzed asymmetric allylic alkylation of indoles

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Article information

DOI
https://doi.org/10.1039/C6OB01354F
Article type
Paper
Submitted
23 Jun 2016
Accepted
07 Jul 2016
First published
07 Jul 2016

Org. Biomol. Chem., 2016,14, 7509-7519

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Chiral N-1-adamantyl-N-trans-cinnamylaniline type ligands: synthesis and application to palladium-catalyzed asymmetric allylic alkylation of indoles

T. Mino, K. Nishikawa, M. Asano, Y. Shima, T. Ebisawa, Y. Yoshida and M. Sakamoto, Org. Biomol. Chem., 2016, 14, 7509 DOI: 10.1039/C6OB01354F

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