Best. TOC Graphic. EVER.

From Acc. Chem. Res., a true gem. You're welcome.

P.S. - If you've never seen it, try the TOC-ROFL Tumblr!

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)?

Gotta Chelate 'Em All

Quick, someone call TOC ROFL; there's a fantastic new abstract graphic in town:

Source: JOC | B. Fischer, Bar-Ilan

Yes, that's Pac-Man, in all his NAMCO glory, chomping on a chelated soft metal ion. Turns out these compounds excel at wrapping up "soft/borderline" metals (Cu, Zn, Pb, Hg, Fe) and stopping radical reactions in their tracks.

Maybe this entry might also complement Derek's "Things I won't work with," since cooking up these (wait for it) methylenediphosphonotetrathioates proceeds as follows: Add super-stoichiometric ethanedithiol to hot bromoform and aluminum salts, and stir in starting material (a bis-phosphoryl-dichloride); heat for 5 days.

P.S. - Don't forget that the two-step process evolves four equivalents of thiirane....yum!