Talk:Macrocyclic stereocontrol

Initial Comments:

The article is reasonably laid out, but needs more examples. Why are the figures so small?

Suggestions:

- Lead: please re-write this. One could argue that remote stereocontrol is actually one of the most surprising aspects of macrocyclic stereocontrol--that stereocenters that are topologically quite remote from the reacting center can apparently direct the stereochemical outcome of the reaction with high fidelity. I see two issues: are macrocycles flopppy? Some seem to be, some aren't, and most we don't know. Floppiness can be estimated by computations. Can a rigid macrocycle give high stereocontrol? Obviously. What about a floppy one? Apparently, they can! What is remarkable is that a small delta G between conformers in the ground state can translate into a large delta delta G dagger in the transition state.

- Consider having explicit cyclooctane and cyclodecane sections. There is basically nothing about their conformational analysis on other pages.

- Have you added links on other pages so that this article is not an orphan?

- What do you mean, "as the structure gets increasingly acyclic"? I would rather say that an "aufbau" way to analyze conformations would be to minimize local interactions like the ones you note, but that this is likely to be stymied by unexpected and subtle interactions between remote substituents.

- Give some examples up front to show that control is possible (like in the lead). I have come to think that the model is dubious at best, but it is also the best thing available.

Eugene Kwan (talk) 19:45, 24 October 2011 (UTC)

Merge proposal
My cursory review is that this article is pretty specialized but not useless. The references are so disappointingly because many are missing titles and doi's. Few refs are to reviews. One solution might be to distribute the contents to various other articles including macrocyclic compound.--Smokefoot (talk) 23:32, 30 January 2024 (UTC)