126686-07-5Relevant academic research and scientific papers
Transition-Metal-Free [4+3]-Cycloaddition of ortho-Quinone Methides and Isomünchnones: Catalytic and Diastereoselective Assembly of Oxa-bridged Oxazocine Scaffolds
Lam, Heather,Qureshi, Zafar,Wegmann, Marcus,Lautens, Mark
, p. 16185 - 16189 (2018)
Cycloadditions are powerful processes to synthesize complex polycyclic scaffolds. Herein, we disclose a [4+3]-cycloaddition between an in situ generated ortho-quinone methide and an isomünchnone to yield oxa-bridged oxazocine cores, generating N2 and H2O as the sole by-products. Using only catalytic amounts of camphorsulfonic acid, it is possible to generate both reactive intermediates in one step, eliminating the need for rhodium catalysts generally employed for isomünchnone formation. Spectroscopic data and X-ray crystallography indicate the formation of the syn diastereomer, with the main side-product arising from a hydrate participating in a competing [4+2]-cycloaddition pathway.
Synthesis of Nitrogen-Containing Polycycles via Rhodium(II)-Induced Cyclization-Cycloaddition and Insertion Reactions of N-(Diazoacetoacetyl)amides. Conformational Control of Reaction Selectivity
Doyle, Michael P.,Pieters, Roland J.,Taunton, Jack,Pho, Hoan Q.,Padwa, Albert,et al.
, p. 820 - 829 (2007/10/02)
A series of diazoacetoacetamides, when treated with a catalytic quantity of a rhodium(II) carboxylate, were found to afford products derived from both a carbonyl ylide intermediate and intramolecular C-H insertion.With 3-(N-(diazoacetoacetyl)amino)propano
SYNTHESIS OF AZA SUBSTITUTED POLYCYCLES VIA RHODIUM (II) CARBOXYLATE INDUCED CYCLIZATION OF DIAZOIMIDES
Padwa, Albert,Hertzog, Donald L.,Chinn, Richard L.
, p. 4077 - 4080 (2007/10/02)
Treatment of several substituted diazoimide derivatives with rhodium (II) carboxylates results in nitrogen-containing cyclic carbonyl ylide formation followed by 1,3-dipolar cycloaddition.
