| 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
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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