38400-84-9Relevant articles and documents
Facile synthesis of libraries of functionalized cyclopropanes and oxiranes using ionic liquids – A new approach to the classical Corey-Chaykovsky reaction
Malunavar, Shruti S.,Sutar, Suraj M.,Prabhala, Pavankumar,Savanur, Hemantkumar M.,Kalkhambkar, Rajesh G.,Aridoss, Gopalakrishnan,Laali, Kenneth K.
supporting information, (2021/09/13)
The potential of [PAIM][NTf2]/BMIM-ILs as a base/solvent in the Corey-Chaykovsky reaction is demonstrated by the facile synthesis of libraries of functionalized cyclopropanes from enones and oxiranes from aldehydes and ketones, at room temperature in respectable isolated yields. To demonstrate their application, the synthesized epoxides were employed as substrates for the synthesis of a library of 2,3-disubstituted quinolines, using [BMIM(SO3H)][OTf]/[BMIM][PF6] as a catalyst/solvent. The potential for recycling/reuse of the IL solvents was also explored.
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.
Tandem oxidation processes for the preparation of functionalized cyclopropanes
Oswald, Magalie F.,Raw, Steven A.,Taylor, Richard J. K.
, p. 3997 - 4000 (2007/10/03)
(Chemical Equation Presented) A novel manganese dioxide-mediated tandem oxidation process (TOP) has been developed which allows the direct conversion of allylic alcohols into cyclopropanes, the intermediate aldehydes being trapped in situ with a stabilized sulfur-ylide. This methodology has been applied successfully to a variety of allylic alcohols and to a formal synthesis of the simple, naturally occurring lignan, (±)-picropodophyllone.
