114663-10-4Relevant academic research and scientific papers
Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1: H -azepines
Craig, Donald,Spreadbury, Samuel R. J.,White, Andrew J. P.
supporting information, p. 9803 - 9806 (2020/09/16)
Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K2CO3 gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines. These undergo highly stereoselective [4+2] cycloaddition reactions with heterodienophiles and arylation/alkenylation under Suzuki conditions.
Synthesis of Enantiopure PZM21: A Biased Agonist of the Mu-Opioid Receptor
Perrey, David,Zhang, Dehui,Nguyen, Thuy,Carroll, F. Ivy,Ko, Mei-Chuan,Zhang, Yanan
, p. 4006 - 4012 (2018/07/30)
PZM21 (1) was recently reported as a biased agonist of the mu-opioid receptor (MOR) with improved antinociceptive effects and reduced side effects compared with traditional opioid-based analgesics. The original synthesis of PZM21 with the desired (S,S) configuration required the separation of a diastereomeric mixture in the final step by using chiral HPLC. A concise synthesis of 1 has now been developed in the enantiomeric pure form starting with commercially available l-alanine and proceeding via a chiral aziridine as a key intermediate. The final product was obtained as the (S,S) diastereomer in seven steps in 22.5 % yield from l-alanine. This synthetic strategy could be readily applied to the development of PZM21 analogues at the thiophenyl position.
Pd(ii)-Catalyzed aerobic 1,2-difunctionalization of conjugated dienes: Efficient synthesis of morpholines and 2-morpholones
Wen, Ke,Wu, Zhengxing,Chen, Buyun,Chen, Jianzhong,Zhang, Wanbin
supporting information, p. 5618 - 5625 (2018/08/17)
A novel and efficient methodology concerning the Pd(ii)-catalyzed intermolecular difunctionalization of conjugated dienes is reported to synthesize a series of functionalized morpholines and 2-morpholones. Widely distributed and easily obtained β-amino alcohols and α-amino acids, as starting nitrogen and oxygen sources, are successfully applied in the difunctionalization of conjugated dienes respectively. The majority of the desired products were obtained in moderate to excellent yields. Oxygen was successfully employed as a terminal oxidant. Further transformation of the generated products allowed for the expansion of structural diversity.
Palladium-catalyzed intramolecular reductive olefin hydrocarbonation: Benzylic hydrogen serving as a new hydrogen donor
Dong, Xu,Cui, Jie,Song, Jian,Han, Ying,Liu, Qing,Dong, Yunhui,Liu, Hui
supporting information, p. 4903 - 4906 (2017/07/11)
A palladium-catalyzed intramolecular hydrocarbonation of unactivated alkenes was achieved, in which toluene is used as a hydrogen donor for the first time. The radical transfer hydrogenation is designed and realized based on the Bond Dissociation Energy (
Lewis acid mediated intramolecular C-O bond formation of alkanol-epoxide leading to substituted morpholine and 1,4-oxazepane derivatives: Total synthesis of (±)-Viloxazine
Ghosh, Priya,Deka, Manash J.,Saikia, Anil K.
, p. 690 - 698 (2016/01/15)
Substituted morpholines have been efficiently synthesised in good yields from nitrogen tethered alkanol-epoxide mediated by boron trifluoride etherate. The methodology has been used for the total synthesis of (±)-viloxazine.
An efficient synthetic approach for N-C bond formation from (S)-amino acids: An easy access to cis-2,5-disubstituted chiral piperazines
Manna, Sudipta Kumar,Panda, Gautam
, p. 18332 - 18338 (2013/10/21)
An efficient synthetic strategy is described for the construction of amino acids derived enantiomerically pure cis-2,5-disubstituted chiral piperazines. Cu-catalyzed spontaneous regioselective ring opening and ring closing of non-activated N-tosyl aziridines as well as Pd-mediated N-C bond formation from N-tosyl halogenated amino-derivatives are the key steps for accessing disubstituted piperazines.
Stereoselective geminal difunctionalization of vinyl arenes mediated by the bromonium ion
Balaji, Pandur Venkatesan,Chandrasekaran, Srinivasan
supporting information, p. 70 - 72 (2014/01/06)
An anti-Markovnikov geminal oxyamination of styrenyl alkenes in an intermolecular fashion using the umpolung strategy mediated by the bromonium ion is reported. Isotope labeling studies confirm the migration of the phenyl group in the semipinacol rearrang
Copper-catalyzed sulfonamides formation from sodium sulfinates and amines
Tang, Xiaodong,Huang, Liangbin,Qi, Chaorong,Wu, Xia,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 6102 - 6104 (2013/07/11)
A new and convenient method for the construction of sulfonamides via a copper-catalyzed oxidative coupling between sodium sulfinates and amines with 1 atm O2 or DMSO as the oxidant was described. This method provides efficient and robust synthesis of functional sulfonamides in good yields and excellent chemoselectivity. And detailed mechanistic studies showed that this transformation may go through a single electron transfer (SET) pathway.
Palladium-catalyzed atom transfer radical cyclization of unactivated alkyl iodide
Liu, Hui,Qiao, Zongjun,Jiang, Xuefeng
supporting information; experimental part, p. 7274 - 7277 (2012/09/25)
A palladium-catalyzed atom transfer cyclization of unactivated alkyl iodide has been developed. A radical chain mechanism has been proposed for this transformation, which might not involve an alkylpalladium intermediate.
Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes
Sequeira, Fatima C.,Chemler, Sherry R.
supporting information, p. 4482 - 4485 (2012/10/29)
A new copper(II) 2-ethylhexanoate-promoted addition of an alcohol and an amine across an alkene (oxyamination) is reported. The alcohol addition is intramolecular, while coupling with the amine occurs intermolecularly. Several 2-aminomethyl morpholines we
