Treading lightly

I think scientists need to approach their research from the standpoint of Ocham’s razor. This way of thinking is by far the best way to analyze complex experimental data where many parameters are interconnected and cause / effect relationships are convoluted. From time to time, I will be posting cases in which Ocham’s razor might not have been applied. But first – what is it? This tool of logic posits that out of several plausible hypotheses, the one with the fewest assumptions is the winner. In other words, the simplest explanation is usually the correct one.

We were discussing an interesting Nature Chemistry paper at our journal club today. The asymmetric phase transfer-catalyzed reaction described by Paton and Smith is billed as a violation of Baldwin’s rules. On a cursory look, it does appear to be an example of the disfavored 5–endo–trig process (see top equation in the graphic below). A theoretical rationale put forth by the authors includes a sophisticated quantum mechanical backing. I like the reaction, but if I were to apply Ocham’s razor here, I would consider a simpler resonance-based explanation shown at the bottom. Here I am using the methoxy substrate (incidentally, one of the better ones in the paper), although we all know that the Curtin-Hammet principle might “rescue” the less fortunate reactants. My goal here is not to say that the more elaborate explanation offered by the authors does not have merit. It is possible that my suggestion is energetically unattractive, but I think it ought to be considered and thoroughly evaluated in addition to the more complex ideas that are being presented. By the way, I have always liked how Eric Carreira refers to Baldwin’s rules as Baldwin’s “suggestions”. One can often avoid violating these “commandments” using resonance structures.