103723-91-7Relevant academic research and scientific papers
Palladium-catalyzed allylic alkylation of carboxylic acid derivatives: N-acyloxazolinones as ester enolate equivalents
Trost, Barry M.,Michaelis, David J.,Charpentier, Julie,Xu, Jiayi
supporting information; experimental part, p. 204 - 208 (2012/02/16)
Triple A: A general asymmetric allylic alkylation of ester enolate equivalents at the carboxylic acid oxidation state is reported. N-Acylbenzoxazolinone-derived enol carbonates were synthesized and employed in the palladium-catalyzed alkylation reaction. The imide products were readily converted into a series of carboxylic acid derivatives without loss of enantiopurity.
Synthesis of polycyclic β-lactams from D-glucose derived chiral template via substrate-controlled radical cyclization
Deshmukh, Abdul Rakeeb A. S.,Jayanthi, Arumugam,Thiagarajan, Kamanan,Puranik, Vedavati G.,Bhawal, Baburao M.
, p. 2965 - 2974 (2007/10/03)
A highly stereoselective and substrate-controlled synthesis of polycyclic β-lactams from D-glucose derived chiral template via intramolecular radical cyclization is described. The cyclization is highly substrate dependant, proceeding via 6-exo and 7-endo heptenyl type radical cyclization with the radical acceptor allyl group at N-1 and the radical progenitor on a sugar moiety, anchored to the β-lactam ring at C-4. The mode of radical cyclization in N-propargyl substrates is highly stereospecific and controlled by the stereochemistry of the β-lactam ring.
A facile synthesis of azidoformate via chloroformate
Wu, Pei-Lin,Su, Chia-Hao,Gu, Yi-Jeng
, p. 271 - 274 (2007/10/03)
This work synthesized chloroformates by slowly adding alcohols into a suspension of trichloromethyl chloroformate, instead of phosgene, along with activated charcoal in tetrahydrofuran. This chloroformylation yielded chloroformates in near quantitative yield. The subsequent reaction between chloroformates and sodium azide in dry acetone produced azidoformates in a high yield.
Palladium Catalysis in Allylic Rearrangements of Propenyl 2-Pyrimidinyl Carbonates to 1-Propenyl-2(1H)-pyrimidinones
Falck-Pedersen, Mette Lene,Benneche, Tore,Undheim, Kjell
, p. 63 - 67 (2007/10/02)
Propenyl 2-pyrimidiyl carbonates have been prepared and found to undergo allylic rearrangement with Pd(0) catalysis under mild conditions to form N-propenyl-2-pyrimidinones.Carbon dioxide is expelled in the reaction.The nature of the phosphine ligands and the substitution pattern in the allylic system affect the isomer product ratios.
Intramolecular 'Ene' Reactions of Transient, Allylic, and Homoallylic C-Nitrosoformate Esters
Kirby, Gordon W.,McGuigan, Henry,McLean, David
, p. 1961 - 1966 (2007/10/02)
Various allylic and homoallylic alcohols have been treated succesively with phosgene and hydroxylamine to form the corresponding N-hydroxycar bamic esters (3).Oxidation of these hydroxamic acid derivatives with sodium or tetraethylammonium periodate in the presence of cyclopentadiene gave the cycloadducts (5) derived from transient allylic and C-nitrosoformate esters (4) and cyclopentadiene.When the cycloadducts were heated in benzene at 80 degree C, or toluene at 111 degree C, they dissociated and the C-nitrosoformate esters underwent intramolecular 'ene' reactions to give hydroxamic acid derivatives having newly formed, five- six- or seven-membered heterocyclic rings.
