Table 1 Self-disproportionation of non-racemic 1a.

From: Understanding the Thalidomide Chirality in Biological Processes by the Self-disproportionation of Enantiomers

Entry

X (% ee)b

Organic solvent

Y (% ee)b

1

21

EtOH (8 mL)

21

2

16

CHCl3/EtOH (2 mL/2 mL)

17

3c

16

DMSO (0.2 mL)

50

4c

19

DMSO (25 μL)

83

  1. aThe (R)-1 sample was prepared by dissolving (S)-1 (2 mg) and (R)-1 (3 mg) in the organic solvent; the initial ee (X% ee) was determined directly at this point. Then, the SDE experiment was carried out upon addition of water (1 mL). The final ee (Y% ee) was determined from the supernatant after 1 h. bThe ee was determined by HPLC using a CHIRALCEL OJ-H column with ethanol as the eluent. cIn the final solution, a substantial amount of precipitate was observed.
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