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

Takashi Mino; Kaho Takaya; Kaito Koki; Natsume Akimoto; Yasushi Yoshida; Yoshio Kasashima; Masami Sakamoto

doi:10.1039/d3ob00224a

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

Org Biomol Chem. 2023 Mar 29;21(13):2775-2778. doi: 10.1039/d3ob00224a.

Authors

Takashi Mino^{1

2

3}, Kaho Takaya¹, Kaito Koki¹, Natsume Akimoto¹, Yasushi Yoshida^{1

2

3}, Yoshio Kasashima⁴, Masami Sakamoto^{1

2}

Affiliations

¹ Graduate School of Engineering, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan. tmino@faculty.chiba-u.jp.
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.

PMID: 36920143
DOI: 10.1039/d3ob00224a

Abstract

We synthesized N-alkyl-N-cinnamoyl amide type phosphine-olefin compounds 1 and found axial chirality in a C(aryl)-N(amide) bond in compounds 1 by HPLC analysis using a chiral stationary phase column. We successfully obtained enantiomeric isomers of 1 and demonstrated the use of (-)-1 for chiral ligands in Pd-catalyzed asymmetric allylic substitution reactions of allylic esters with indoles (up to 97% ee).