114491-32-6Relevant academic research and scientific papers
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.
Ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation and 1,3-dipolar cycloaddition reactions of α-diazo ketones
Zhou, Cong-Ying,Yu, Wing-Yiu,Che, Chi-Ming
, p. 3235 - 3238 (2007/10/03)
equation presented The ruthenium porphyrin-catalyzed reactions of diazo ketones with π-unsaturated compounds via carbonyl ylide formation/cycloaddition cascade exhibit product yields and selectivities comparable to the analogous reactions with dirhodium c
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
