OC tidbits #7

Mose et al. (Jørgensen lab) [Nature Chemistry]

There are whole bunch of messy electrocyclic reactions in the paper and nice projections explaining diastereoselectivity. They made me nostalgic about reading OC texbooks.

mose_et_al

Hugelshofer and Magauer [JACS]

Want something even cooler, here’s a dyotropic reaction! Characterizing the side-products must have been a lot of fun. As well as monitoring the progress (the major undesired product had the same Rf as the starting material, and good luck with crude NMR). Heads up from amphoteros.

hugelshofer

Hall, Roche, and West [OL]

Was this reversible photo-switch discovered by accidentally shining a wrong UV lamp onto the final product?  The authors say it was expected. [Note: UVA = 350 nm; UVC = 254 nm]. TOC graphic:

ol-2016-03689z_0005

Chen et al. (Yu lab) [ACIE]

OK, enough electrocyclic reactions. Here’s some C-H activation work from Jin-Quan Yu lab. From [phthalimide-protected] alanine to [phthalimide-protected] substituted phenylalanines in one step! The conditions are somewhat peculiar though. A lot of silver (and quite a lot of palladium) was consumed for this to happen.

yu

Shi, Jiang, and Tian [JOC]

Tellurium is not very popular among chemists (and even less among anybody else for that matter), so each successful use of it is worth attention. The authors of this paper managed to find an application for sodium hydrotelluride. As an excuse they wrote this last sentence of discussion: ‘Reduction of the α-azido ketone 31 with PPh3, as in the Staudinger reduction, followed by stirring in air could not deliver 34 in our hands.’
tellurium
Another unusual thing in the paper is the open call for collaborations: ‘For now, gram scale of 30 and more than 100 mg of 34 [12,12′-azo-13,13′-diepi-Ritterazine N] are available for any interested collaborators.’ I felt obliged to spread the word.
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