Issue 7, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of δ- and ε-keto esters of 1,1′-binaphthalen-2-ols with an oligoether tether as the 2′-substituent: application to the synthesis of (−)-malyngolide

Masamitsu Date,a   Yasufumi Tamai,*b   Tetsutaro Hattori,*a   Hideki Takayama,a   Yoshinori Kamikuboa  and  Sotaro Miyano*a  

* Corresponding authors

a Department of Biomolecular Engineering, Graduate School of Engineering, Tohoku University, Aramaki-Aoba 07, Aoba-ku, Sendai 980-8579, Japan

b Department of Material Chemistry and Engineering, College of Engineering, Nihon University, Tokusada-Nakagawara 1, Tamura-machi, Koriyama 963-8642, Japan

Abstract

Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of podand-type δ- (3,4) and ε-keto esters (5,6) are achieved in the presence of MgBr2·OEt2 with up to 97 and 82% optical yields, respectively, by using 2′-[3-(2-methoxyethoxy)propoxy]-1,1′-binaphthalen-2-ol as the chiral auxiliary. The 1,8-asymmetric inductive Grignard reaction has been advantageously utilized in the key step of a synthesis of (−)-malyngolide.

Graphical abstract: Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of δ- and ε-keto esters of 1,1′-binaphthalen-2-ols with an oligoether tether as the 2′-substituent: application to the synthesis of (−)-malyngolide

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Article information

DOI
https://doi.org/10.1039/B100497M
Article type
Paper
Submitted
15 Jan 2001
Accepted
22 Feb 2001
First published
15 Mar 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 645-653

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Efficient 1,8- and 1,9-asymmetric inductions in the Grignard reaction of δ- and ε-keto esters of 1,1′-binaphthalen-2-ols with an oligoether tether as the 2′-substituent: application to the synthesis of (−)-malyngolide

M. Date, Y. Tamai, T. Hattori, H. Takayama, Y. Kamikubo and S. Miyano, J. Chem. Soc., Perkin Trans. 1, 2001, 645 DOI: 10.1039/B100497M

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