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Synthesis 2007(19): 2973-2978  
DOI: 10.1055/s-2007-983892
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Yohji Nakatsuji*a, Yoshio Nakaharab, Katsumori Nagamiyab, Yuki Itohb, Kentaro Uesugib, Naohisa Ishidaa, Masahiro Muraokaa, Toshiyuki Kidab, 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;
Further Information

Publication History

Received 8 September 2006
Publication Date:
11 September 2007 (online)

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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