Thursday, February 12, 2015

Beautiful Chemistry: Hoye's HDDA + Napth Trap

Every so often, a reaction behaves so well that you just publish the crude NMR spectrum.
Professor Tom Hoye's HDDA* reaction, first reported in 2012, apparently fits the bill rather well, wouldn't you say?

From Org. Lett. 2015, ASAP.

Amazing - heat up a heavily conjugated triyne for 2 days, and it just does one thing, reproducibly and immaculately. I wonder whether Hoye and his group have any further tricks up their sleeve to try and control the diastereo  enantioselectivity of that sweet new quaternary center...time will tell.

*Please allow me touch of professional jealousy - this reaction opened up so many different questions for the Hoye group that they've published 10 manuscripts on it in just the last 3 years. Damn.

**Perhaps I've developed a love affair with barrelenes. Hmm.

Thanks for the catch, Per-Ola!


  1. As another lover of interesting Diels-Alder reactions (specifically to make 2.2.2 bicycles), I think the most compelling examples in this paper are not the very clean naphyl traps but but rather, trapping with benzene or other tethered benzyl groups. Thank you for highlighting this paper.

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