Is it possible to convert from enantiomer to diastereoisomer?

Discussion created by ywzhao98 on Mar 13, 2011

Recently I synthesized one molecule (5-member ring, with one asymmetric carbon connecting to a hydroxyl group) which was proved to be an enantiomers and have be separated by asymmetric column. However, I found two enantioomers (caused by the -OH) can interchangeable. After about 10 days' placement at room tempeature, they totally turned into diastereoisomers(50/50). I am not familiar with this field. What I want to ask is if it is possible for this conversion? Does anybody know some similar cases to this? Would you please provide me some referecne for reading?


In addition, I want to discuss the mechanism of this conversion. Should it be a thermal process or chemical reaction process (via the carbonium cation formation of the asymmetric carbon)?


Thanks for your discussion. And you advices are of great help.