Facile Synthesis of C2-Symmetric Chiral Crown Ethers with Two Reactive Hydroxymethyl Groups

Yohji Nakatsuji; Yoshio Nakahara; Katsumori Nagamiya; Yuki Itoh; Kentaro Uesugi; Naohisa Ishida; Masahiro Muraoka; Toshiyuki Kida; Mitsuru Akashi

doi:10.1055/s-2007-983892

PAPER

Facile Synthesis of C ₂-Symmetric Chiral Crown Ethers with Two Reactive Hydroxymethyl Groups

Yohji Nakatsuji*^a, Yoshio Nakahara^b, Katsumori Nagamiya^b, Yuki Itoh^b, Kentaro Uesugi^b, Naohisa Ishida^a, Masahiro Muraoka^a, Toshiyuki Kida^b, Mitsuru Akashi*^b
^a Nanomaterials Microdevices Research Center and Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, 5-16-1 Omiya, Asahi-ku, Osaka 535-8585, Japan
Fax: +81(6)69572135; e-Mail: nakatsuji@chem.oit.ac.jp;
^b Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita 565-0871, Japan
Fax: +81(6)68797359; e-Mail: akashi@chem.eng.osaka-u.ac.jp;

Abstract

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Abstract

Two C ₂-symmetric chiral crown ethers, (2S,12S)-2,12-bis(hydroxymethyl)-2,12-dimethyl-18-crown-6 and (2R,9R)-2,9-bis(hydroxymethyl)-2,9-dimethyl-18-crown-6 were synthesized from a chiral subunit, [(4S)-2,2,4-trimethyl-1,3-dioxolane-4-yl]methanol, at high enantiomeric purity over several steps. This synthetic method offers the potential to construct a variety of C ₂-symmetric chiral crown ethers using diverse combinations of building blocks.

Key words

C ₂-symmetric chiral crown ethers - chiral subunit - lipase QL - optical resolution - C-pivot carbons

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References

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Facile Synthesis of C 2-Symmetric Chiral Crown Ethers with Two Reactive Hydroxymethyl Groups

Facile Synthesis of C ₂-Symmetric Chiral Crown Ethers with Two Reactive Hydroxymethyl Groups