109384-74-9Relevant academic research and scientific papers
Stereodivergent Rhodium(III)-Catalyzed cis-Cyclopropanation Enabled by Multivariate Optimization
Piou, Tiffany,Romanov-Michailidis, Fedor,Ashley, Melissa A.,Romanova-Michaelides, Maria,Rovis, Tomislav
supporting information, p. 9587 - 9593 (2018/08/07)
The design of stereodivergent transformations is of great interest to the synthetic community as it allows funneling of a given reaction pathway toward one stereochemical outcome or another by only minor adjustments of the reaction setup. Herein, we present a physical organic approach to invert the sense of induction in diastereoselective cyclopropanation of alkenes with N-enoxyphthalimides through rhodium(III) catalysis. Careful parametrization of catalyst-substrate molecular determinants allowed us to interrogate linear-free energy relationships and establish an intuitive and robust statistical model that correlates an extensive number of data points in high accuracy. Our multivariate correlations-steered mechanistic investigation culminated with a robust and general diastereodivergent cyclopropanation tool where the switch from trans- to cis-diastereoinduction is attributed to a mechanistic dichotomy. Selectivity might be determined by the flexibility of rhodacyclic intermediates derived from ring-opened versus -unopened phthalimides, induced by both their respective ring size and the Sterimol B1 parameter of the CpX ligand on rhodium.
Highly regioselective tandem formal substitution and decarboxylation of 2-acyl-1-chlorocyclopropanecarboxylates with sodium sulfinates
Zhu, Yuequan,Gong, Yuefa
, p. 3436 - 3442 (2016/06/06)
This article reported a highly regioselective tandem formal nucleophilic substitution and decarboxylation reaction of alkyl 2-acyl-1-chlorocyclopropanecarboxylates with sodium sulfinates under basic conditions. Actually, alkyl 2-acyl-1-chlorocyclopropanec
Organic-catalyst-mediated cyclopropanation reaction
Papageorgiou, Charles D.,Ley, Steven V.,Gaunt, Matthew J.
, p. 828 - 831 (2007/10/03)
A catalytic ammonium ylide based cyclopropanation process forms trans-disubstituted cyclopropanes in good yield upon reaction with electron-deficient alkenes (see scheme; EWG = electron-withdrawing group). The reaction is also highly enantioselective when
Reactivity of Bifunctional Alkenes with Diazomethane
Reddy, D. Bhaskar,Sarma, M. Rajagopala,Padmaja, A.,Padmavathi, V.
, p. 23 - 32 (2007/10/03)
The cycloaddition of diazomethane to 1-aroyl-2-arylsulfonylethenes (1) and 1,2-bis(arylsulfonyl)ethenes (IV) under different conditions led to a variety of pyrazolines and pyrazoles. The reactivity of pyrazolines was also studied by pyrolysis, nitrosation and acylation.
A Novel Phase - Transfer Catalysed Cycloaddition of Carbonyl-Stabilized Sulfur Ylides to Vinylic Sulfones
Reddy, D. Bhaskar,Reddy, P. S.,Reddy, B. V.,Reddy, P. A.
, p. 74 - 75 (2007/10/02)
In our current studies on the chemistry and synthetic utility of carbonyl stabilized sulfur ylides, we have found that the cycloaddition of dimethylsulfonium phenacylides to aryl vinyl sulfones to be a useful general approach to 1-arylsulfonyl-2-aroylcyclopropanes 3.
