Thursday, February 13, 2014

Cyclobutanone Déjà vu

Didn't I just see that reaction? [rubs eyes]

From the laboratory of Prof. Nicolai Cramer (EPF Lausanne) comes some really neat examples of cyclobutanone C-C activation. Just mix with ~2 mol% of cationic Rh(I), and presto! Out comes a [3.1.2] bicyclo product reminiscent of several neuroactive natural products.

Oftentimes, a catalytic reaction will go gangbusters, but will stubbornly refuse all attempts at asymmetric induction. Apparently not so here - Cramer reports the asymmetric version in ACIEE about two weeks after the initial Organometallics report!

Angew. Chem. Int. Ed. 2014, ASAP
Organometallics 2014, ASAP
Honestly, I might never have noticed, except the TOC graphics for both are nearly identical: a comic pair of orange scissors "snipping" apart the cyclobutanone ring.

So, readers, what's your take? Can't wait to see this reaction applied to a challenging target? Or, a strange choice of synthetic "least publishable units" (LPUs)?


  1. With having first author papers ever more important for getting jobs and fellowships, it may not be altogether a case of LPU, but a way of giving both his students what they need to proceed in their careers.

  2. From my point of view the Organometallics report is mainly focused on the interesting new zwitterionic bis-phospholane ligands whereas the ACIEE paper is focused on the cyclobutanone C-C activation.

    So yes similar reactions, silimar TOC graphics but completely different goals.

  3. OMG, Please look at the Supporting Information file, They used the same Spectra data (1H, 13C-NMR, HPLC….) for 2 papers (with same compound). So what happened here? They are not do experiments? Or just do 1 exp. for 1 paper and write another with the same data??? Or one of them is fake? We need an explanation!
    Might be I just using Water as catalyst and take the same NMR data for all Starting material and products (from ACIEE paper or Organometallics ) an then submit to another journal??