Back in 2006, together with Ryan Hili we stumbled upon amphoteric aziridine aldehydes that defied logic due to a kinetic barrier imposed on the amine/aldehyde condensation. Ever since then we have been looking at expanding the scope of this chemistry, which allowed us to better understand how to put a wide palette of amphoteric reagents to good use. Together with Zhi He and Adam Zajdlik we have put together an account that sums up our work to date. Here is a link to this paper (it came out today).

http://pubs.acs.org/doi/abs/10.1021/ar400210c

Below is a recent picture of my lab back in December, on our way to a wild night of playing ping-pong (a special thanks to Sai for taking the photo!):

There is a growing interest in boron-containing peptide and small molecule inhibitors of serine and threonine proteases (and a host of other targets). This interest drives research aimed at new methods of synthetic installation of the boroamine functional group. In the past, I mentioned some of my lab’s work in this area. My former PhD student Zhi He (now a postdoctoral fellow with Tim Jamison at MIT) and Adam Zajdlik (currently a second year PhD student in my lab) have laid a foundation for making boron-containing amines using amphoteric reagents. We are actively investigating this area and are collaborating with the lab of Ben Cravatt. We are also beginning what will hopefully be a productive collaborative relationship with Anacor in Palo Alto, CA. In July of this year Adam is going to San Francisco, where he will use his methods of boroamine synthesis in collaboration with Anacor.

I pay attention to other labs’ advances in this area and want to mention an excellent Org Lett paper by Bernard Carboni and colleagues from Rennes, France. This work describes an imaginative new way to access alpha-boryl amines using [3,3]-sigmatropic rearrangement. Below is the main idea this work is based on. Given the widespread availability of vinyl boronate building blocks, the reaction constitutes a promising new way of installing B-C-N motifs into organic molecules. 

http://pubs.acs.org/doi/abs/10.1021/ol401016x?mi=vx3ktd&af=R&page

Hi all, I am glad that one of the readers reminded me about a classic work by Jack Dunitz. In addition to my personal response, I decided to post a link so that everyone can see it and save in their folders of “important papers”. 

http://onlinelibrary.wiley.com/doi/10.1002/chem.19970030115/abstract

The title says it all: a contradiction to what the Linclau study suggests. However, the Dunitz paper is primarily a crystallographic study, which is an important distinction. One comment: people no longer come up with really great titles. There is a monumental inscription in the title of the Dunitz contribution: “Organic Fluorine Hardly Ever Accepts Hydrogen Bonds”!