Being resourceful

My lab has been interested in challenging hemiaminals to do things they are typically not known for. Below is an example from Kim’s lab, showing how one can be really resourceful with hemiaminals. I have always been a fan of this sort of chemistry and, earlier today, rediscovered this cool sequence while going through my “paper vault”. Access to either of the two amino alcohol diastereomers is at stake in this chemistry. The syn diastereomer is accessible directly from the hemiaminal by way of conjugate addition. What about the anti version? In order to get that, you oxidize the hemiaminal into the corresponding hydroperoxy species, which transfers its oxygen atom to the nearby olefin under basic conditions the way any hydroperoxide would do. While this chemistry is now several years old, it does attest to how useful hemiaminals can be.

gg

http://www.sciencedirect.com/science/article/pii/S0957416611005362

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