Issue 20, 2015
From the journal:

Organic & Biomolecular Chemistry

BINOL-Al catalysed asymmetric cyclization and amplification: preparation of optically active menthol analogs†

Hisanori Itoh,ab   Hironori Maeda,a   Shinya Yamada,a   Yoji Hori,*a   Takashi Mino*b  and  Masami Sakamotob  

* Corresponding authors

a Takasago 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

We report a highly selective asymmetric ring-closing ene reaction catalysed by aluminum complexes with chiral BINOL. This reaction yields optically active 6-membered cyclized alcohols from unsaturated aldehydes, with good diastereo- and enantioselectivities. Asymmetric amplification of this reaction was investigated by varying the ee of the BINOL employed in the catalyst.

Graphical abstract: BINOL-Al catalysed asymmetric cyclization and amplification: preparation of optically active menthol analogs

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Article information

DOI
https://doi.org/10.1039/C5OB00433K
Article type
Paper
Submitted
04 Mar 2015
Accepted
12 Apr 2015
First published
27 Apr 2015

Org. Biomol. Chem., 2015,13, 5817-5825

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BINOL-Al catalysed asymmetric cyclization and amplification: preparation of optically active menthol analogs

H. Itoh, H. Maeda, S. Yamada, Y. Hori, T. Mino and M. Sakamoto, Org. Biomol. Chem., 2015, 13, 5817 DOI: 10.1039/C5OB00433K

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