Application

No.136
Optical Resolution for Alcohols and Thiols
A1984 (S)-5-Allyl-2-oxabicyclo[3.3.0]oct-8-ene (1) 1g

Compound 1, developed by Nemoto et al., is an optical resolving agent for alcohols and thiols. Using this reagent under a simple protocol, chiral alcohols and thiols can be easily obtained with high optical purity. For example, 1 reacts with racemic alcohols in benzene or dichloromethane in the presence of an acid catalyst to form a mixture of diastereomers 2. These diastereomers can then be separated on the thin layer chromatography (TLC), and easily isolated by silica gel column chromatography. Methanolysis of the isolated compounds 2 in the presence of an acid catalyst affords the chiral alcohols. Moreover, it is possible to recover 3 and reuse 1 derived from 3. Since this process proceeded under a mild condition, it has been expected to be a useful method to obtain chiral alcohols and thiols.

References

1) Novel optical resolving agent
a) K. Sakamoto, H. Nemoto, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.), 2007, 65, 626; b) H. Nemoto, H. Tsutsumi, S. Yuzawa, X. Peng, W. Zhong, J. Xie, N. Miyoshi, I. Suzuki, M. Shibuya, Tetrahedron Lett., 2004, 45, 1667.
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