128947-27-3Relevant academic research and scientific papers
Synthesis of N-vinyloxazolidinones and morpholines from amino alcohols and vinylsulfonium salts: Analysis of the outcome's dependence on the N-protecting group by nanospray mass spectrometry
Yar, Muhammad,Fritz, Sven P.,Gates, Paul J.,McGarrigle, Eoghan M.,Aggarwal, Varinder K.
supporting information; experimental part, p. 160 - 166 (2012/02/04)
The effect of the nature of the N-protecting group on 1,2-amino alcohols in annulation reactions with diphenylvinylsulfonium triflate has been investigated. Although tosyl and sulfinamide groups give morpholines in high yields, the use of N-Cbz leads to a high-yielding synthesis of N-vinyloxazolidinones. The reactions were monitored by nanospray MS/MS, which revealed why reactions are successful and the fate of reactive intermediates in the unsuccessful reactions.
Enamide-benzyne-[2 + 2] cycloaddition: Stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions
Feltenberger, John B.,Hayashi, Ryuji,Tang, Yu,Babiash, Eric S.C.,Hsung, Richard P.
supporting information; experimental part, p. 3666 - 3669 (2011/02/25)
Image Presented Benzyne-[2 + 2] cycloadditions with enamides are described. This effort led to the development of a highly stereoselective tandem [2 + 2] cycloaddition-pericyclic ring-opening-intramolecular-N-tethered-[4 + 2] cycloaddition for rapid assembly of nitrogen heterocycles.
Synthetic Studies on the Key Component of the New Generation of Quinolonecarboxylic Acid, DU-6859. 2. Asymmetric Synthesis of (1R,2S)-2-Fluorocyclopropylamine
Akiba, Toshifumi,Tamura, Osamu,Hashimoto, Masaru,Kobayashi, Yuko,Katoh, Tadashi,et al.
, p. 3905 - 3914 (2007/10/02)
The title synthesis was achieved by featuring diastereoface-selective cyclopropanation of (4R,5S)-4,5-diphenyl-3-vinyl-2-oxazolidinone and its related compounds, the chiral conformationally rigid N-vinylcarbamates, with zinc-monofluorocarbenoid, followed
Synthesis of Optically Active Butenolides via Chromium Alkoxycarbene Complexes: Total Synthesis of (+)-Tetrahydrocerulenin and Two Butenolides from the Marine Sponge Plakortis lita
Miller, Michael,Hegedus, Louis S.
, p. 6779 - 6785 (2007/10/02)
Optically active butenolides were synthesized from the corresponding cyclobutanones, derived from the photolysis of chromium alkoxycarbene complexes and optically active ene-carbamates.The cyclobutanones were oxidized (Baeyer-Villiger) to the corresponding lactones, and subsequent base-induced elimination of the β-oxazolidinone ring provided optically active butenolides efficiently.The butenolides were utilized in the syntheses of (+)-tetrahydrocerulenin and two marine natural products.
Palladium(II)-Assisted Difunctionalization of Monoolefins: Total Synthesis of (+)-Negamycin and (-)-5-epi-Negamycin
Masters, John J.,Hegedus, Louis S.
, p. 4547 - 4554 (2007/10/02)
(+)-Negamycin and (-)-5-epi-negamycin were synthesized by a process involving the palladium(II)-assisted alkylation of an optically active ene carbamate followed by carbonylative coupling to a trialkylvinyltin.The synthesis of (+)-negamycin was completed in 15 steps with an overall yield of 13percent.The synthesis of (-)-5-epi-negamycin was completed in 12 steps with an overall yield of 20percent.In preparing these compounds, a highly diastereoselective reduction of an unsaturated ketone and an efficient intramolecular Mitsunobu reaction were also carried out.
Asymmetric Synthesis of (1R,2S)-2-Fluorocyclopropylamine, the Key Intermediate of the New Generation of Quinolonecarboxylic Acid, DU-6859
Tamura, Osamu,Hashimoto, Masaru,Kobayashi, Yuko,Katoh, Tadashi,Nakatani, Kazuhiko,et al.
, p. 3487 - 3490 (2007/10/02)
The title synthesis was achieved by featuring diastereoface selective cyclopropanation of (4R,5S)-4,5-diphenyl-3-vinyl-2-oxazolidinone, the chiral and conformationally rigid N-vinylcarbamate, with zincmonofluorocarbenoid followed by hydrogenolysis of form
Palladium(II)-Assisted Dialkylation and Alkylation/Acylation of Optically Active Ene Carbamates via Trialkylorganostannane Cross-Coupling and Carbonylative Coupling Processes
Masters, John J.,Hegedus, Louis S.,Tamariz, Joaquin
, p. 5666 - 5671 (2007/10/02)
Alkylation of benzyl vinyl carbamate and propene with the anions of diethyl methylmalonate or dimethyl malonate in the presence of palladium(II) chloride, followed by cross-coupling or carbonylative cross-coupling with organostannanes, effected an overall dialkylation or alkylation/acylation of the monoolefin substrate.Complete control of stereochemistry in this palladium(II)-assisted reaction was observed using optically active ene carbamates affording β-amino-unsaturated keto esters in good chemical yields and excellent optical purity.
Synthesis of optically active ene carbamates from chromium carbene complexes: Use in palladium(II)-assisted synthesis of relays to (+)-thienamycin
Montgomery, John,Wieber, Gary M.,Hegedus, Louis S.
, p. 6255 - 6263 (2007/10/02)
Attempts to prepare optically active chromium carbene complexes containing the oxazolidinone moiety led instead to an efficient and general synthesis of optically active ene carbamates. One of these has been subjected to palladium(II)-assisted carboacylat
