5817-70-9Relevant articles and documents
Iridium-catalyzed regiospecific and stereospecific allylic amination for the syntheses of α,β-unsaturated γ-amino esters and the bifurcation of the reaction pathway leading to the formation of oxazolidin-2-ones
Lee, Jun Hee,Lee, Sang-Gi
, p. 2922 - 2927 (2013)
A pair of iridium-catalyzed regiospecific and stereospecific reactions of the carbonates of γ-hydroxy α,β-unsaturated esters were developed. The reaction pathways are strongly affected by the choice of amines employed. A diverse range of γ-substituted α,β-unsaturated γ-amino esters were prepared in excellent yields with various amine nucleophiles such as benzylamine, diallylamine, morpholine, aniline and N-methylaniline. Substitution at the γ-position was well tolerated, encompassing alkyl, aryl and heteroaryl substituents. Enantioenriched (E)-α,β-unsaturated γ-amino esters could also be synthesized from the corresponding enantioenriched allylic carbonates with complete chirality transfer. In sharp contrast, a series of 3,4-disubstituted oxazolidin-2-ones were obtained by using allylamine as a nucleophile.
N-Aryl and N-Alkyl Carbamates from 1 Atmosphere of CO2
Chen, Ming-Yu,Choe, Yoong-Kee,Choi, Jun-Chul,Fukaya, Norihisa,Hamura, Satoshi,Koizumi, Hiroki,Matsumoto, Kazuhiro,Matsumoto, Seiji,Shigeyasu, Shinji,Takeuchi, Katsuhiko,Yuan, Hao-Yu
supporting information, p. 18066 - 18073 (2021/12/08)
We have successfully isolated and characterized the zinc carbamate complex (phen)Zn(OAc)(OC(=O)NHPh) (1; phen=1,10-phenanthroline), formed as an intermediate during the Zn(OAc)2/phen-catalyzed synthesis of organic carbamates from CO2, amines, and the reusable reactant Si(OMe)4. Density functional theory calculations revealed that the direct reaction of 1 with Si(OMe)4 proceeds via a five-coordinate silicon intermediate, forming organic carbamates. Based on these results, the catalytic system was improved by using Si(OMe)4 as the reaction solvent and additives like KOMe and KF, which promote the formation of the five-coordinated silicon species. This sustainable and effective method can be used to synthesize various N-aryl and N-alkyl carbamates, including industrially important polyurethane raw materials, starting from CO2 under atmospheric pressure.
Methoxycarbonylation of Alkyl-, Cycloalkyl-, and Arylamines with Dimethyl Carbonate in the Presence of Binder-Free Zeolite
Khazipova, A. N.,Khusnutdinov, R. I.,Mayakova, Yu. Yu.,Shchadneva, N. A.
, p. 1228 - 1235 (2020/10/02)
Abstract: Methyl N-alkyl-, N-cycloalkyl-, and N-arylcarbamates were synthesized by reaction of the correspondingamines with dimethyl carbonate in the presence of binder-free FeHY zeolite. Theoptimal conditions (reactant ratio, amount of the catalyst, temperature,reaction time) were found to afford the target products with high yields.
O-Alkyl S-(Pyridin-2-yl)carbonothiolates: Operationally Simple and Highly Nitrogen-Selective Reagents for Alkoxy Carbonylation of Amino Groups
Hashimoto, Yoshimitsu,Morita, Nobuyoshi,Suzuki, Tomoyuki,Tamura, Osamu,Tanaka, Kosaku
, p. 899 - 902 (2020/05/28)
Amino groups are selectively protected in good yields by reaction with O-Alkyl S-(pyridin-2-yl)carbonothiolates in an appropriate solvent at room temperature in air. Even glucosamine, which contains multiple hydroxyl groups, is selectively N-protected in methanol.
