On early mornings without coffee (but with boron)

Yesterday morning I was doodling on a piece of paper, thinking about Zhi’s synthesis of alpha boryl aldehydes. These molecules offer a nice entry into boron-containing intermediates (I blogged about them in July). Of course, “B” stands for “boron”…

It was early in the a.m., I did not have my coffee yet, and I somehow typed bromine (Br) instead of boron (B)… But then it occurred to me: “crap, there is something weirdly familiar here!”. I started digging into our old papers and I found one by my former PhD student Larissa Krasnova from 2006. She developed this nice hydrazone formation:

http://pubs.acs.org/doi/abs/10.1021/ol061695x?prevSearch=%255BContrib%253A%2Bkrasnova%255D&searchHistoryKey=

If you compare her work to our boryl aldehyde synthesis, there is an interesting parallel in terms of what migrates and what is around the migrating group… Mechanisms are different, but still:

Image

Whenever there are interesting ways of comparing the incomparable, I always go back to the lessons taught to us by Roald Hoffmann of Cornell. I refer to isolobal relationships, of course.

In our case there is no isolobal relationship, just a lack of caffeine, but still… Interesting.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s