59724-53-7Relevant academic research and scientific papers
Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
Yang, Hui,Zheng, Wen-Hua
supporting information, p. 16177 - 16180 (2019/11/03)
A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.
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.
Thiyl radical-mediated cyclization of ω-alkynyl O-tert-butyldiphenylsilyloximes
Shibata, Nina,Tsuchiya, Takahisa,Hashimoto, Yoshimitsu,Morita, Nobuyoshi,Ban, Shintaro,Tamura, Osamu
supporting information, p. 3025 - 3034 (2017/04/10)
ω-Alkynyl O-tert-butyldiphenylsilyloximes, upon treatment with odorless 4-tert-butylbenzenethiol in the presence of azobisisobutyronitrile (AIBN) in refluxing benzene, underwent addition of a thiyl radical to the alkynyl group followed by radical cyclizat
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.
Synthesis of 1,2-amino alcohols via catalytic C-H amidation of sp3 methyl C-H bonds
Kang, Taek,Kim, Heejeong,Kim, Jeung Gon,Chang, Sukbok
supporting information, p. 12073 - 12075 (2014/12/11)
Herein a new synthetic route to 1,2-amino alcohols is presented by using C-H amidation of sp3 methyl C-H bonds as a key step. Readily available alcohols were employed as starting materials after converting them to removable ketoxime chelating g
Enantioselective organocatalytic michael/aldol sequence: Anticancer natural product (+)-trans-dihydrolycoricidine
McNulty, James,Zepeda-Velazquez, Carlos
supporting information, p. 8450 - 8454 (2014/08/18)
A total synthesis of the anticancer natural product (+)-trans- dihydrolycoricidine is reported from α-azidoacetone and cinnamaldehyde precursors. Key elements include an asymmetric organocatalytic sequence proceeding by a regiospecific secondary-amine-catalyzed synMichael addition followed by an intramolecular aldol reaction. The sequence results in the formation of an advanced intermediate, containing three stereogenic centers, in one step which and was converted into the title compound in eight steps.
Metal-free oxidative coupling of amines with sodium sulfinates: A mild access to sulfonamides
Zhao, Jinwu,Xu, Jingxiu,Chen, Jiaxi,Wang, Xiaoqin,He, Minghua
, p. 64698 - 64701 (2015/04/27)
A practical and mild procedure for the preparation of sulfonamides through TBAI-catalyzed oxidative coupling of amines with sodium sulfinates using TBHP as an oxidant was presented. A variety of amines and sodium sulfinates could go through the transformation, without impacting the hydroxyl group. This journal is
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
Iron(III)-promoted aza-prins-cyclization: Direct synthesis of six-membered azacycles
Carballo, Ruben M.,Ramirez, Miguel A.,Rodriguez, Matias L.,Martin, Victor S.,Padron, Juan I.
, p. 3837 - 3840 (2007/10/03)
A new iron(III) halide-promoted aza-Prins cyclization between γ,δ-unsaturated tosylamines and aldehydes provides six-membered azacycles in good to excellent yields. The process is based on the consecutive generation of γ-unsaturated-iminium ion and further nucleophilic attack by the unsaturated carbon-carbon bond. Homoallyl tosylamine leads to trans-2-alkyl-4-halo-1-tosylpiperidine as the major isomer. In addition, the alkyne aza-Prins cyclization between homopropargyl tosylamine and aldehydes gives 2-alkyl-4-halo-1-tosyl-1,2,5,6-tetrahydropyridines as the only cyclic products.
