62708-41-2Relevant academic research and scientific papers
A Transient-Directing-Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes
Deng, Ruohan,Engle, Keary M.,Erbay, Tu??e G.,Li, Zi-Qi,Liu, Peng,Oxtoby, Lucas J.,Tran, Van T.
supporting information, p. 8885 - 8890 (2020/04/15)
Metal-coordinating directing groups have seen extensive use in the field of transition-metal-catalyzed alkene functionalization; however, their waste-generating installation and removal steps limit the efficiency and practicality of reactions that rely on their use. Inspired by developments in asymmetric organocatalysis, where reactions rely on reversible covalent interactions between an organic substrate and a chiral mediator, we have developed a transient-directing-group approach to reductive Heck hydroarylation of alkenyl benzaldehyde substrates that proceeds under mild conditions. Highly stereoselective migratory insertion is facilitated by in situ formation of an imine from catalytic amounts of a commercially available amino acid additive. Computational studies reveal an unusual mode of enantioinduction by the remote chiral center in the transient directing group.
Rhodium-catalyzed intramolecular hydroacylation of 1,2-disubstituted alkenes for the synthesis of 2-substituted indanones
Yuan, Jing,Liu, Chong,Chen, Yan,Zhang, Zhenfeng,Yan, Deyue,Zhang, Wanbin
, p. 269 - 277 (2018/12/05)
The intramolecular hydroacylation of 1,2-disubstituted alkenes was considered to be a challenging task due to the side reactions resulted from the lack of additional substituent at 1-position and the low activity caused by the steric hindrance of substituent at 2-position, and an asymmetric version has not been considered possible due to problems associated with the racemization of the products. We have partially solved these problems. Catalyzed by an activated diphosphine-Rh complex and reacted in a selected dihalogenated solvent, the intramolecular hydroacylation of o-(2-arylvinyl)benzaldehydes provided the corresponding 2-aryl-1-indanones in high yields, and its asymmetric variant using o-(2-alkylvinyl)benzaldehydes afforded chiral 2-alkyl-1-indanones in high yields and with moderate enantioselectivities.
Photoreactivity of α-Tetrasubstituted Arylketones: Production and Asymmetric Tautomerization of Arylenols
Henin, Francoise,M'Boungou-M'Passi, Athanase,Muzart, Jacques,Pete, Jean-Pierre
, p. 2849 - 2864 (2007/10/02)
In the presence of catalytic amounts of optically active aminoalcohols, the irradiation of α-disubstituted indanones, tetralones and propiophenones bearing at least one hydrogen in the γ-position led to Norrish type II cleavage compounds which were obtained with enantiomeric excesses reaching 89percent.The influence of the reaction conditions (temperature, wavelength of the UV light and nature of the aminoalcohol) has been analyzed.
1,7-Electrocyclisation and Carbene Reactions of o-Alkenylaryldiazoalkanes: The Effect of Alkene Configuration on the Mode of Reaction
Munro, David P.,Sharp, John T.
, p. 849 - 858 (2007/10/02)
The 1,7-8?-electron electrocyclisation of o-alkenylaryldiazoalkanes (1) to give 1H-2,3-benzodiazepines (3) takes place readily for substrates with a cis-hydrogen atom at the cyclisation site, but is blocked by phenyl or methyl groups at that position.Such
