Sunday, 24 February 2013

This week, I have been mostly reading...

It's been a few days since #chemclub kicked off on Twitter, so I thought I'd round up a few highlights ahead of the week to come. If you're not sure what I'm on about, have a gander here.

First up is a cute total synthesis of teurilene, contributed by @Total_Synthesis (a very handy resource, I might add). It's centred on a cascade of intramolecular epoxide openings, which creates three furans with nice stereoselectivity and good yield. I liked it!

For the methodology lovers, a paper from Toste using PTC to perform asymmetric fluorination of phenols in decent yields and enantiomeric excesses. The products aren't simply fluorophenols, but undergo dearomatisation to quinones, or dimerisation to bridged bicyclics. They use the latter reaction to generate a natural product-like compound in basically one step. The yield isn't great, but it's still pretty nice I think.

From @craigdc1983 comes an oldie but a goody, bringing Ockham's razor to bear upon the widely-held and -taught idea of secondary orbital interactions, which are invoked to explain selectivity in cycloadditions. They argue that the classic experiments used to justify this model are not as convincing as you'd think, and that selectivity is adequately accounted for in terms of more mundane effects - dispersion forces, solvation, and so on. It's not a quick read, but definitely worth spending some time on.
Craig also unleashed a broadside on hyperconjugation as an explanation for the anomeric effect. Perhaps he can launch the #BlogSyn of physical organic theory?

Speaking of BlogSyn, @V_Saggiomo has a bone to pick with Ingerman et al. regarding full characterisation of compounds. Given that they're funded by the US Army I might stay out of this one... In any case, apparently Vittorio is planning to repeat the work and make the data freely available. Mighty kind.
Finally, my own contribution, a paper from Nature Chemistry by Hergenrother and co-workers looking at ways to generate stereochemical diversity in a few steps. @vinylogous has already highlight this over at Not the Lab (h/t @stuartcantrill), so I'll say no more.
Thanks to everyone who contributed. Please do keep it up! Post interesting, amusing, or controversial papers (new and old) to #chemclub for discussion.

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