Journal Article Assembly of a Benzo-Fused Bridged Ketone Scaffold from 1,5,10-Enediynes through One-Pot Ruthenium-Catalyzed Cyclization/Iodine-Mediated Oxidative Ring Expansion

Yamamoto, Yoshihiko  ,  Nishimura, Kei-ichiro  ,  Mori, Shota  ,  Shibuya, Masatoshi

56 ( 20 )  , pp.5494 - 5497 , 2017-05-08 , Wiley
In the presence of a cationic Ru catalyst, 1,6-diynes bearing a terminal styryl moiety underwent [2+2+2] cyclization to produce dehydrobiphenylenes fused with a five-membered ring. Although the cycloadducts were unstable toward purification, their one-pot iodine-mediated ring expansion successfully afforded unprecedented bridged ketone products containing a benzo-fused bicyclo[3.2.1] framework.

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