152303-03-2Relevant academic research and scientific papers
Asymmetric Allylation/RCM-Mediated Synthesis of Fluorinated Benzo-Fused Bicyclic Homoallylic Amines As Dihydronaphthalene Derivatives
Sedgwick, Daniel M.,Barrio, Pablo,Simón, Antonio,Román, Raquel,Fustero, Santos
, p. 8876 - 8887 (2016)
Enantiomerically enriched fluorinated benzo-fused bicyclic homoallylic amines have been synthesized through an asymmetric allylation/ring closing metathesis (RCM) sequence. This sequence has been carried out using α-trifluoromethylstyrene derivatives as key intermediates, synthesized by microwave radiation. The great deactivating effect exerted by such substituents has been brought to light by a comparative study.
Enantioselective N-Heterocyclic Carbene Catalyzed Cyclopentene Synthesis via the β-Azolium Ylide
Scott, Lydia,Nakano, Yuji,Zhang, Changhe,Lupton, David W.
, p. 10299 - 10303 (2018)
Herein we report the cycloisomerization of electron-poor 1,5-dienes via the β-azolium ylide to give enantioenriched cyclopentenes. The reaction is mediated by a chiral N-heterocyclic carbene (NHC) catalyst, exploits readily available substrates, has good generality (17 examples), and displays excellent enantioselectivity (mostly >94:6). Studies demonstrating the viability of a related dynamic kinetic resolution are reported, as are those with alternate tethers and derivatizations.
Hydroacylation of 2-vinyl benzaldehyde systems: An efficient method for the synthesis of chiral 3-substituted indanones
Kundu, Kousik,McCullagh, James V.,Morehead Jr., Andrew T.
, p. 16042 - 16043 (2007/10/03)
Asymmetric rhodium-catalyzed hydroacylation has been utilized in the synthesis of 3-substituted indanones with high conversions and enantioselectivity. The hydroacylation reaction of 2-vinyl benzaldehyde had been previously reported to give a low yield of indanone and an unidentified product. We have identified this compound as a dimer of the starting material. Substitution at the α-position of the 2-vinyl benzaldehyde substrates blocks the competitive dimerization reaction and allows the reaction to proceed with yields generally greater than 90%. Utilization of BINAP as a chiral ligand results in good chemical yields and enantioselectivity greater than 95% in most cases. Copyright
Copper(I) Salt-Mediated Arylation of Phosphinyl-Stabilized Carbanions and Synthetic Application to Heterocyclic Compounds
Minami, Toru,Isonaka, Takeshi,Okada, Yoshiharu,Ichikawa, Junji
, p. 7009 - 7015 (2007/10/02)
The copper-mediated reaction of phosphinyl-stabilized carbanions 2a-c with aryl halides 1a-i in DMF or HMPA produced (arylmethyl)phosphonates 3-11 in good yields.Similar treatment of N-(2-iodophenyl)- and N-(2-iodophenyl)-N-methyl-α-(diethoxyphosphinyl)ac
