118917-60-5Relevant academic research and scientific papers
A tandem process for the synthesis of β-aminoboronic acids from aziridines with haloamine intermediates
Park, Subin,Koo, Jangwoo,Kim, Weonjeong,Lee, Hong Geun
, p. 3767 - 3770 (2022/04/07)
An unprecedented synthetic strategy is devised to generate β-aminoboronic acids from aziridines via a sequential process involving 1,2-iodoamine formation and radical borylation under light irradiation. A variety of aziridines including multiply substituted aziridines have been successfully employed as synthetic precursors, expanding their synthetic utility compared to previous methods. Mechanistic studies suggest that the boron source plays a unique role in the borylation step, and in the formation of haloamine intermediates.
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.
A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines
Aubineau, Thomas,Cossy, Janine
supporting information, p. 7419 - 7423 (2018/12/11)
The diastereoselective synthesis of various substituted morpholines has been achieved from vinyloxiranes and amino-alcohols under sequential Pd(0)-catalyzed Tsuji-Trost/Fe(III)-catalyzed heterocyclization. Using the same strategy, 2,6-, 2,5-, and 2,3-disubstituted as well as 2,5,6- and 2,3,5-trisubstituted morpholines were obtained in good to excellent yields and diastereoselectivities.
Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines
Li, Kangnan,Weber, Alexandria E.,Tseng, Luke,Malcolmson, Steven J.
, p. 4239 - 4242 (2017/08/23)
The 1,3-diamine motif appears in numerous complex molecules, yet there are few methods for the stereoselective construction of this moiety. Herein, we demonstrate a stereocontrolled synthesis of 1,3-diamines, which bear up to three contiguous stereogenic centers, through benzylic ring-opening of aziridines with 2-azaallyl anion nucleophiles. Reactions proceed efficiently (yield up to 95%), diastereoselectively (dr up to >20:1), site selectively, and enantiospecifically to deliver products with differentiated amino groups.
Cis -1,2-Aminohydroxylation of Alkenes Involving a Catalytic Cycle of Osmium(III) and Osmium(V) Centers: OsV(O)(NHTs) Active Oxidant with a Macrocyclic Tetradentate Ligand
Sugimoto, Hideki,Mikami, Akine,Kai, Kenichiro,Sajith,Shiota, Yoshihito,Yoshizawa, Kazunari,Asano, Kaori,Suzuki, Takeyuki,Itoh, Shinobu
, p. 7073 - 7082 (2015/08/03)
Catalytic activity of [OsIII(OH)(H2O)(L-N4Me2)](PF6)2 (1: L-N4Me2 = N,N′-dimethyl-2,11-diaza-[3,3](2,6)pyridinophane) in 1,2-cis-aminohydroxylation of alkenes with sodium N-chloro-4-methylbenzenesulfonamide (chloramine-T) is explored. Simple alkenes as well as those containing several types of substituents are converted to the corresponding 1,2-aminoalcohols in modest to high yields. The aminoalcohol products have exclusively cis conformation with respect to the introduced -OH and -NHTs groups. The spectroscopic measurements including cold mass spectroscopic study of the reaction product of complex 1 and chloromine-T as well as density functional theory (DFT) calculations indicate that an oxido-aminato-osmium(V) species [OsV(O)(NHTs)(L-N4Me2)](PF6)2 (2) is an active oxidant for the aminohydroxylation. The DFT calculations further indicate that the reaction involves a [3 + 2] cycloaddition between 2 and alkene, and the regioselectivity in the aminohydroxylation of unsymmetrical alkenes is determined by the orientation that bears less steric hindrance from the tosylamino group, which leads to the energetically more preferred product isomer.
Efficient and regioselective ring-opening of arylaziridines with alcohols, thiols, amines and N-heteroaromatic compounds using sulphated zirconia
Llaveria, Josep,Espinoza, Araceli,Negrón, Guillermo,Isabel Matheu,Castillón, Sergio
supporting information; experimental part, p. 2525 - 2529 (2012/06/18)
Sulphated zirconia is an efficient catalyst for the regioselective ring-opening of aryl-substituted aziridines. This heterogeneous catalyst can be used several times without loss of activity and is compatible with a variety of acid sensitive and slightly basic nucleophiles.
Catalyst-free process for the synthesis of 5-aryl-2-oxazolidinones via cycloaddition reaction of aziridines and carbon dioxide
Dou, Xiao-Yong,He, Liang-Nian,Yang, Zhen-Zhen,Wang, Jing-Lun
supporting information; experimental part, p. 2159 - 2163 (2010/10/21)
A simple approach for facile synthesis of 5-aryl-2-oxazolidinones in excellent regioselectivity from aziridines under compressed CO2 conditions was developed in the absence of any catalyst and organic solvent. The reaction outcome was found to be tuned by subtly adjusting CO2 pressure. The adduct formed in situ of aziridine and CO2 is assumed to act as a catalyst in this reaction, which was also studied by means of in situ FT-IR technique.
Tin-free radical addition of acyloxymethyl to imines
Yamada, Ken-Ichi,Nakano, Mayu,Maekawa, Masaru,Akindele, Tito,Tomioka, Kiyoshi
supporting information; experimental part, p. 3805 - 3808 (2009/07/01)
(Chemical Equation Presented) Acyloxymethyl radicals were generated from the corresponding iodomethyl esters and successfully underwent addition to the C=N bond of N-Ts, N-PMP, and N-Dpp imines by the action of dimethylzinc or triethylborane. Ethyl acetate, toluene, and benzene as well as dichloromethane were suitable solvents. The utility of acyloxymethyl radicals as a hydroxymethyl anion equivalent was highlighted by the facile hydrolysis of the acyloxy moiety of the adducts to give the corresponding amino alcohol derivatives in good to high yield.
Asymmetric synthesis of α-amino aldehydes from sulfinimine (N-sulfinyl imine)-derived α-amino 1,3-dithianes. Formal synthesis of (-)-2,3-trans-3,4-cis-dihydroxyproline
Davis, Franklin A.,Ramachandar, Tokala,Chai, Jing,Skucas, Eduardas
, p. 2743 - 2746 (2007/10/03)
Hydrolysis of sulfinimine-derived N-sulfinyl α-amino 1,3-dithianes with aqueous 1,3-dibromo-5,5-dimethylhydantoin affords the corresponding N-tosyl α-amino aldehydes in good yield and high enantiomeric purity. These aldehydes can be reduced to amino alcoh
Asymmetric radical addition of ethers to enantiopure N-p-toluenesulfinyl aldimines, mediated by dimethylzinc-air
Akindele, Tito,Yamamoto, Yasutomo,Maekawa, Masaru,Umeki, Hiroyuki,Yamada, Ken-Ichi,Tomioka, Kiyoshi
, p. 5729 - 5732 (2007/10/03)
(Diagram presented) Asymmetric radical addition of ethers to enantiopure aromatic N-p-toluenesulfinyl aldimines has been achieved. The requisite radicals were generated by dimethylzinc-air. Lewis acid activation of the N-p-toluenesulfinyl aldimines follow
