Unveiling Chiral Discrimination in Helically Chiral Diastereomers through Reversed Phase HPLC: Insight from Induced Herical Chiralty

These results indicate that

1. The methylene chain length of the reversed phase column is important for the separation,
2. Both of the column methylene chain and the diastereomer's methylene chain are straight and interact in a liner way with each other,
3. A Methylene chain of the column must interact with the two chiral positions (one is the position that tells the helical chirality of the diastereomer and the other is that of methyl branching) of the diastereomer simultaneously so that it gets the two information of the chirality of the diastereomer at the same time.

Now, a new question "How can one chiral information of the diastereomer be transmitted to the other interaction position through the methylene chain?" arises.

Here, I would like to propose an idea of "induced helically chiral methylene chain".

In conclusion, the normally achiral reversed phase column is changed into a chiral column by the interaction with the eluate.

ACKNOWLEDGEMENT

The author would like to dedicate this paper to his two deceased mentors, Dr. Masanao Matsui and Dr. Kenji Mori.