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)?

3 comments:

  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.

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  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.

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  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??

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