In yesterday’s issue of Nature, we published a paper from Amir Hoveyda‘s and Mark Snapper’s groups at Boston College. The paper describes a simple metal-free catalyst that can perform enantioselective catalytic silylations on a variety of meso 1,2-diols, obtaining mono-protected chiral diols.
The chemical yields and enantiomeric selectivities of the reactions are very good – in some cases, excellent – although the reaction times are long (2-3 days). Relatively large amounts of the catalyst are required, but this is not a problem as the catalyst is simple to prepare from inexpensive starting materials. Clearly this is just the beginning of a development process and more active catalysts will be forthcoming.
These kinds of catalysts could shave several steps off synthetic routes to prostaglandin analogues, unnatural nucleosides, and neocarzinostatin analogues, which currently require a number of chemical transformations and an enzymatic de-acylation to obtain a key building block. By shortening the synthetic route, the amount of chemical waste produced can be minimized and the amount of time needed to make the molecule can be dramatically reduced. Denmark concludes the News & Views article by saying that
this procedure is likely to have a significant impact on the efficiency and cost of constructing single-enantiomer products. Most importantly, however, this report demonstrates the creative power of synthetic chemistry to build simple organic catalysts that mimic and ultimately surpass, biological catalysts – especially for non-biological transformations.
Collaborations between two well-known organic chemistry labs aren’t extremely common, and Hoveyda talked about this phenomenon on our ‘Authors’ page:
Hoveyda says the synthetic organic chemistry field has traditionally been wary of two principal investigators sharing credit on single papers. “The culture almost discourages it,” he says. Early on, colleagues warned Snapper that working with a more senior researcher could hurt his career. But their partnership has been fruitful; the two have received joint grants from the National Institutes of Health since 1997 and have published about 20 papers together. “The reason this collaboration has been so successful is that neither of us cares who gets the credit,” Hoveyda adds.
If you’d like to learn more about the research, Hoveyda was interviewed on this week’s Nature Podcast (he also appears on the recent chemistry podcast). And if you’re in San Francisco at the Fall ACS Meeting next week, you can see Yu Zhao talk about the work on Monday afternoon.
Joshua Finkelstein (Associate Editor, Nature)