126686-05-3Relevant academic research and scientific papers
Bimolecular Cycloaddition Reactions of Isomuenchnones Derived from the Rhodium(II) Catalyzed Cyclization of Diazo Pyrrolidinones
Padwa, Albert,Hertzog, Donald L.
, p. 2589 - 2600 (1993)
Treatment of diazo substituted pyrrolidinones with a catalytic amount of rhodium(II) acetate in refluxing benzene results first in the formation of a rhodium carbenoid which then cyclizes onto the neighboring carbonyl oxygen to produce an isomuenchnone ri
π-Facial Diastereoselection in [3 + 2]-Cycloadditions of Isomuenchnone Dipoles
Padwa, Albert,Prein, Michael
, p. 6842 - 6854 (2007/10/03)
The Rh(II)-catalyzed reaction of 1-[diazo(methoxycarbonyl)acetyl]-2-oxopyrrolidine derivatives led to the formation of ring-fused isomuenchnone betaines which are trapped with various dipolarophiles to give the corresponding [3 + 2]-cycloadducts in excellent yield. The cycloaddition reaction proceeded with high levels of diastereoselectivity leading to the predominant formation of the exo dipolar cycloadduct. The influence of substituents on the stereoselectivity of the reaction was investigated. Diastereotopic facial selectivity by the dipolarophile on the mesoionic betaine was found to depend upon the nature of the stereogenic center. Inclusion of substituents at any position of the fused five-membered ring was found to enhance exo selectivity. Isomuenchnone dipoles derived from pyrrolidinones containing a carboalkoxy substituent in the 5-position of the ring afforded mainly exo-syn cycloadducts. In contrast, when a methyl group was present at the 3-position of the pyrrolidinone ring, the facial selectivity was reversed with the exo-anti adduct being the major product. A computational study was carried out to rationalize the observed product distribution.
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.
