Abstract
The solid diastereoisomeric mixture4a+4b was obtained via the asymmetric Michael addition reaction of phenylthioalcohol with liquid epimeric mixture 5-(-)-bornyloxy-2(5H)-furanone3a+3b, which was prepared by reaction of the natural abundant chiral auxiliary borneol 2 with 5-hydroxy-2(5H)-furanone 1. The two diastereoisorners4a +4b were separated by means of preferential cyrstallization, which gave one optically pure compound4b with de > 98 %. The absolute configuration of4b was established by X-ray crystallography. The method provided a new efficient route for utilizing natural chiral auxiliaries and preparing optically pure diastereoisomeric compounds based on liquid epimers.
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Project supported by the National Natural Science Foundation of China.
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Cui, J., Du, B. & Chen, Q. Synthesis and crystal structure of a novel chiral compound prepared from (-)-borneol as a natural chiral auxiliary. Sc. China Ser. B-Chem. 41, 65–70 (1998). https://doi.org/10.1007/BF02875559
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DOI: https://doi.org/10.1007/BF02875559