Issue 106, 2014
From the journal:

RSC Advances

Highly selective aluminium-catalysed intramolecular Prins reaction for l-menthol synthesis†

H. Itoh,ab   H. Maeda,a   S. Yamada,a   Y. Hori,*a   T. Mino*b  and  Masami Sakamotob  

* Corresponding authors

a Taksasago International Corporation 4-11, Nishi-Yawata 1-Chome, Hiratsuka City, Kanagawa 254-0073, Japan
E-mail: yoji_hori@takasago.com

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

Abstract

An aluminium complex bearing 2-cyclohexyl-6-phenylphenol afforded (5R)-n-isopulegol from (R)-citronellal via the intermolecular Prins reaction with an exceptionally high diastereoselectivity. Using this reaction, L-menthol was obtained with an excellent diastereoselectivity.

Graphical abstract: Highly selective aluminium-catalysed intramolecular Prins reaction for l-menthol synthesis

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Article information

DOI
https://doi.org/10.1039/C4RA12470G
Article type
Communication
Submitted
16 Oct 2014
Accepted
11 Nov 2014
First published
11 Nov 2014

RSC Adv., 2014,4, 61619-61623

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Highly selective aluminium-catalysed intramolecular Prins reaction for L-menthol synthesis

H. Itoh, H. Maeda, S. Yamada, Y. Hori, T. Mino and M. Sakamoto, RSC Adv., 2014, 4, 61619 DOI: 10.1039/C4RA12470G

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