51220-85-0Relevant articles and documents
Nitroxyl Catalysts for Six-Membered Ring Bromolactonization and Intermolecular Bromoesterification of Alkenes with Carboxylic Acids
Moriyama, Katsuhiko,Kuramochi, Masako,Tsuzuki, Seiji,Fujii, Kozo,Morita, Takeshi
supporting information, p. 268 - 273 (2021/01/09)
We developed a nitroxyl-catalyzed bromoesterification of alkenes with bromo reagents, which includes a six-membered ring bromolactonization of alkenyl carboxylic acids catalyzed by AZADO as the nitroxyl radical catalyst, and an intermolecular bromoesterification of alkenes with carboxylic acids using NMO as the N-oxide catalyst. We also accomplished a remote diastereoselective bromohydroxylation via an AZADO-catalyzed six-membered ring bromolactonization and a subsequent ring cleavage reaction with alkylamines to furnish ?-bromo-δ-hydroxy amides with high diastereoselectivity.
Direct Intramolecular Aminoboration of Allenes
Yang, Chun-Hua,Han, Meng,Li, Wenyan,Zhu, Ningning,Sun, Zhenzhen,Wang, Junjie,Yang, Zhantao,Li, Yue-Ming
supporting information, p. 5090 - 5093 (2020/07/15)
Direct intramolecular aminoboration of sulfonamidoallenes was realized using BCl3 as a boron source. The reactions benefited from the interaction between BCl3 and sulfonamides and provided a variety of borylvinyl heterocycles in good isolated yields. When chiral substrates were involved in the reactions, high stereoselectivity was observed, as can be ascertained by single-crystal X-ray diffraction experiments. Derivatization of the thus-obtained borylvinyl compounds proceeded readily, and different functionalities could be obtained via oxidation, halogenation, and Suzuki coupling reactions.
Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex
Yudasaka, Masaharu,Shimbo, Daisuke,Maruyama, Toshifumi,Tada, Norihiro,Itoh, Akichika
, p. 1098 - 1102 (2019/05/16)
The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.
Synthesis of Optically Active 2,3-Disubstituted Indoline -Derivatives through Cycloaddition Reactions between Benzynes and α,β-Unsaturated γ-Aminobutyronitriles
Ikawa, Takashi,Sumii, Yuta,Masuda, Shigeaki,Wang, Ding,Emi, Yuto,Takagi, Akira,Akai, Shuji
, p. 530 - 536 (2018/01/17)
We report a method for synthesizing optically active 2,3-disubstituted indolines by the cycloaddition reaction of benzynes with various 4-[(4-toluenesulfonyl)amino]-(E)-but-2-enenitriles, which are readily prepared from the corresponding l -amino acid der
Stereoselective Synthesis of 1,2-trans-Diamines Using the Three-Component Borono-Mannich Condensation – Reaction Scope and Mechanistic Insights
Norsikian, Stéphanie,Beretta, Margaux,Cannillo, Alexandre,Auvray, Marie,Martin, Amélie,Retailleau, Pascal,Iorga, Bogdan I.,Beau, Jean-Marie
, p. 1940 - 1951 (2017/04/21)
The Petasis borono-Mannich (PBM) process with easily accessible N-protected α-amino aldehydes produces 1,2-trans-diamines diastereoselectively with an enantiomeric excess up to 98 %. The protecting group on the nitrogen atom had a decisive influence on bo
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.
Guided desaturation of unactivated aliphatics
Voica, Ana-Florina,Mendoza, Abraham,Gutekunst, Will R.,Fraga, Jorge Otero,Baran, Phil S.
scheme or table, p. 629 - 635 (2012/09/08)
The excision of hydrogen from an aliphatic carbon chain to produce an isolated olefin (desaturation) without overoxidation is one of the most impressive and powerful biosynthetic transformations for which there are no simple and mild laboratory substitutes. The versatility of olefins and the range of reactions they undergo are unsurpassed in functional group space. Thus, the conversion of a relatively inert aliphatic system into its unsaturated counterpart could open new possibilities in retrosynthesis. In this article, the invention of a directing group to achieve such a transformation under mild, operationally simple, metal-free conditions is outlined. This 'portable desaturase' (Tz o °Cl) is a bench-stable, commercial entity (Aldrich, catalogue number L510092) that is facile to install on alcohol and amine functionalities to ultimately effect remote desaturation, while leaving behind a synthetically useful tosyl group.
The effect of substituents on the chiral solvating properties of (S)-1,6-dialkylpiperazine-2,5-diones
Malavasic, Crt,Stanovnik, Branko,Wagger, Jernej,Svete, Jurij
experimental part, p. 1364 - 1371 (2011/11/29)
The effect of substituents on the chiral solvating properties of 13 different (S)-1,6-dialkylpiperazine-2,5-diones (S)-1a-m and five (3S,6S)-1,3,6-trialkyl analogues (S,S)-1n-r was studied by NMR in CDCl 3 with methyl (RS)-N-benzoylleucinate (R
A modified synthetic approach to optically pure benzoxazepines from amino acid precursors using intramolecular buchwald-hartwig C-O bond-formation reaction
Bhattacharya, Debleena,Behera, Ashok,Hota, Sandip K.,Chattopadhyay, Partha
, p. 585 - 592 (2011/04/12)
Palladium-catalyzed intramolecular aryl etherification reaction using bulky binaphthylphosphane ligand is shown to be a convenient method for the synthesis of seven-membered heterocycles. Application of this methodology to a naturally occurring proteinoge
Regioselective ring-opening of amino acid-derived chiral aziridines: An easy access to cis-2,5-disubstituted chiral piperazines
Samanta, Krishnananda,Panda, Gautam
supporting information; experimental part, p. 189 - 197 (2011/10/08)
An efficient four-step synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino-acid-based aziridines is described. The key steps in this strategy are the highly regioselective boron trifluoride diethyl etherate (BF3·OEt2)-mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochloride followed by Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. The pied piperazines: A four-step efficient synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino acid-based aziridines is described. The key reaction steps are the highly regioselective BF3·OEt2 mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochlorides, followed by a Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. Copyright
