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Figure 1
Whereas reaction of the (S,S)-epoxide gives only the (1R,2S)-diol product, the (R,R)-epoxide gives both (1R,2S)- and (1S,2R)-products. The key product differentiating step in the case of the (S,S)-epoxide is selective hydrolysis of the alkyl­ated intermediate formed by reaction of the (S,S)-epoxide at C-1 over that formed by reaction at C-2. Note the stereochemistry of the alkylated intermediates depends on that of the starting epoxide (there are two possible isomers of the alkylated intermediate for each substrate).

IUCrJ
Volume 5| Part 4| July 2018| Pages 373-374
ISSN: 2052-2525
https://doi.org/10.1107/S2052252518007005