15267-27-3Relevant academic research and scientific papers
Cyclopropanation of olefins with nitromethane
Bonge, Hanne Therese,Hansen, Tore
, p. 55 - 58 (2008/03/27)
A procedure for the use of nitromethane as an iodonium ylide precursor has been developed. Electron-rich olefins are cyclopropanated with nitromethane in the presence of bis(acetoxy)iodobenzene, a base and a Rh(II) catalyst to provide nitrocyclopropanes i
"Instant methylide" modification of the Corey-Chaykovsky cyclopropanation reaction
Ciaccio, James A.,Aman, Courtney E.
, p. 1333 - 1341 (2007/10/03)
Treatment of various electron-deficient alkenes in DMSO with stable, dry, equimolar mixtures of either Me3S(O)I/KOt-Bu or Me 3S(O)I/NaH cleanly afforded the corresponding substituted cyclopropanes in good yields and short reaction ti
An Expedient and Practical Method for the Synthesis of A Diverse Series of Cyclopropane α-Amino Acids and Amines
Wurz, Ryan P.,Charette, Andre B.
, p. 1262 - 1269 (2007/10/03)
A practical synthesis for the preparation of a diverse series of cyclopropane α-amino acids is described. Nitrocyclopropane carboxylates can be readily prepared through treatment of α-nitroesters and iodobenzene diacetate or α-nitro-α-diazoesters with a R
NITROCYCLOPROPANES FROM NITRODIAZOMETHANES. PREPARATION AND REACTIVITY
O'Bannon, P. E.,Dailey, William P.
, p. 7341 - 7358 (2007/10/02)
Nitrodiazo compounds cyclopropanate electron rich alkenes in the presence of rhodium(II) acetate.The yields and diastereoselectivities are dependent on both the alkene and the nitrodiazo precursor.Nitrocyclopropanecarboxylates undergo ring opening, reduct
S-Ethenylsulfoximine Derivatives. Reagents for Ethylenation of Protic Nucleophiles
Johnson, Carl R.,Lockard, James P.,Kennedy, Eugene R.
, p. 264 - 271 (2007/10/02)
The preparation of S-vinyl and S-(2-substituted)ethenyl derivatives of sulfoximines is described.Vinyl-, (2-phenylethenyl)-, (2,2-diphenylethenyl)-, (2-methyl-1-propenyl)-, (dimethylamino)phenyloxosulfonium fluoroborates were found to undergo an addition-elimination reaction sequence with protic nitrogen and carbon nucleophiles, resulting in ethylenation of the nucleophile and N,N-dimethylbenzenesulfinamide.Primary amines gave aziridines, enamines gave cyclopropyl derivatives of iminium salts or pyrrolidinium salts, anions of active methylene compounds gave dihydrofurans and/or cyclopropanes, and anions of nitroalkanes gave cyclic nitronic esters and/or nitrocyclopropanes.In several cases vinyl salts were generated in situ from β-methoxyoxosulfonium salts.Treatment of (-)-(S)-dimethylamino)phenyl(trans-2-phenylethenyl)oxosulfonium fluoroborate with methyl cyanoacetate in methanol containing sodium methoxide gave, in 81percent yield, (+)-(1S,2R)-methyl 1-cyano-2-phenylcyclopropanecarboxylate of 25.5percent optical purity.The same salt upon treatment with methyl nitroacetate gave, in 95percent yield, methyl 4-phenyl-3-isoxazolinecarboxylate 2-oxide with 33percent enantiomeric excess.Cyclopropanes were formed upon treatment of S-methyl-S-(trans-2-phenylethenyl)-N-(p-tolylsulfonyl)sulfoximine with anions of active methylene compounds.
