114491-32-6Relevant articles and documents
Rhodium(II)-catalyzed enantioselective synthesis of troponoids
Murarka, Sandip,Jia, Zhi-Jun,Merten, Christian,Daniliuc, Constantin-G.,Antonchick, Andrey P.,Waldmann, Herbert
supporting information, p. 7653 - 7656 (2015/06/25)
We report a rhodium(II)-catalyzed highly enantioselective 1,3-dipolar cycloaddition reaction between the carbonyl moiety of tropone and carbonyl ylides to afford troponoids in good to high yields with excellent enantioselectivity. We demonstrate that α-diazoketone-derived carbonyl ylides, in contrast to carbonyl ylides derived from diazodiketoesters, undergo [6+3] cycloaddition reactions with tropone to yield the corresponding bridged heterocycles with excellent stereoselectivity. Decisive dipoles: In the rhodium(II)-catalyzed asymmetric 1,3-dipolar cycloaddition of tropone with carbonyl ylides, a programmable chemoselective reaction with the keto group or the 6 π system of tropone was controlled by the substrate (see scheme). The developed method enables the synthesis of complex products in highly enantiomerically enriched form.
Tandem cyclization-cycloaddition reaction of rhodium carbenoids. Scope and mechanistic details of the process
Padwa,Fryxell,Zhi
, p. 3100 - 3109 (2007/10/02)
Treatment of 1-diazo-2,5-pentanediones with rhodium(II) carboxylates affords cyclic six-ring carbonyl ylide dipoles. These species undergo facile 1,3-dipolar cycloaddition with both electron-deficient and electron-rich dipolarophiles. In certain cases 2:1
