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When HgCl 2 was added to a diastereomeric mixture of cis- and trans-(4S)-limonene 1,2-epoxide, the Hg(II) ions stereoselectively complexed to the cis epoxide, enabling ring opening by water. The resulting mercuric salt could be demetalated by treatment with NaBH 4 , giving a mixture of diastereomeric (1S,2S,4S)- and (1R,2R,4S)-diols. The remaining trans-(4S)-epoxide was obtained in...
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