22621-98-3Relevant academic research and scientific papers
Direct use of allylic alcohols and allylic amines in palladium-catalyzed allylic amination
Jing, Jiangyan,Huo, Xiaohong,Shen, Jiefeng,Fu, Jingke,Meng, Qinghua,Zhang, Wanbin
supporting information, p. 5151 - 5154 (2017/07/12)
Allylic alcohols and allylic amines were directly utilized in a Pd-catalyzed hydrogen-bond-activated allylic amination under mild reaction conditions in the absence of any additives. The cooperative action of a Pd-catalyst and a hydrogen-bonding solvent is most likely responsible for its high reactivity. The catalytic system is compatible with a variety of functional groups and can be used to prepare a wide range of linear allylic amines in good to excellent yields. Furthermore, this methodology can be easily applied to the one-step synthesis of two drugs, cinnarizine and naftifine, on a gram scale.
Rhodium/Yanphos-Catalyzed Asymmetric Interrupted Intramolecular Hydroaminomethylation of trans-1,2-Disubstituted Alkenes
Chen, Caiyou,Jin, Shicheng,Zhang, Zhefan,Wei, Biao,Wang, Heng,Zhang, Kai,Lv, Hui,Dong, Xiu-Qin,Zhang, Xumu
supporting information, p. 9017 - 9020 (2016/08/05)
The first interrupted asymmetric hydroaminomethylation reaction was developed. The challenging trans-1,2-disubstituted olefins were employed as substrates, and a series of valuable chiral pyrrolidinones and pyrrolidines were obtained in high yields with high regioselectivities and excellent enantioselectivities. Several synthetic transformations were conducted, demonstrating the high synthetic utility of our method. A creative route for the synthesis of vernakalant and Enablex was also developed.
Aerobic direct C-H arylation of nonbiased olefins
Gigant, Nicolas,B?ckvall, Jan-E.
supporting information, p. 4432 - 4435 (2015/01/08)
An efficient ligand-promoted biomimetic aerobic oxidative dehydrogenative cross-coupling between arenes and nonbiased olefins is presented. Acridine as a ligand was found to significantly enhance the rate, the yield, and the scope of the reaction under ambient oxygen pressure, providing a variety of alkenylarenes via an environmentally friendly procedure.
Stereoselective halocyclization of alkenes with n-acyl hemiaminal nucleophiles
Liu, Na,Wang, Hao-Yuan,Zhang, Wei,Jia, Zhi-Hong,Guzei, Ilia A.,Xu, Hua-Dong,Tang, Weiping
, p. 805 - 809 (2013/11/06)
Halocyclization of alkenes was realized using N-acylhemiaminal nucleophiles. High diastereoselectivity could be achieved for the formation of three stereogenic centers in this halogen-mediated cyclization reaction. We also demonstrated that enantioselecti
Substrate-directable heck reactions with arenediazonium salts. The regio- and stereoselective arylation of allylamine derivatives and applications in the synthesis of naftifine and abamines
Prediger, Patricia,Barbosa, Lais Ferreira,Genisson, Yves,Correia, Carlos Roque Duarte
experimental part, p. 7737 - 7749 (2011/12/01)
The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the car-bonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.
Highly Stereoselective Route to (E)-Allyl Amines via Vinyltri-n-butylphosphonium Salts (Schweizer Reaction)
Meyers, A. I.,Lawson, Jon P.,Carver, David R.
, p. 3119 - 3123 (2007/10/02)
The reaction of vinyltri-n-butylphosphonium salts, aldehydes, and sodiophthalimide in THF gave good yields of the allylic phthalimides with high E stereoselectivity (75-100percent).The use of the vinyltriphenylphosphonium salts (Schweizer reaction) gave the allyl phthalimide with the Z isomer predominating.A study of the phthalimide cation and the effect of added lithium salt showed some reversal in the olefin geometry but in general the selectivity was only 3:1
