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Synfacts 2005(3): 0303-0303  
DOI: 10.1055/s-2005-921611
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Planar Chiral Cyclic Ether

Contributor(s): Yasuhiro Uozumi, Toshimasa Suzuka
K. Tomooka*, N. Komine, D. Fujiki, T. Nakai, S. Yanagitsuru
Tokyo Institute of Technology, Japan
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

A discovery of the first example of purely planar chiral cyclic ether 1 was reported. Enantiomerically enriched ether was prepared by a kinetic resolution of racemic compound 1. Thus, the kinetic resolution of rac-1 with asymmetric hydroboration using (+)-Ipc2BH in THF afforded almost enantiopure (R)-1 (>98% ee) in 43% yield (eq. 1).