4765-28-0Relevant academic research and scientific papers
Acylative Kinetic Resolution of Alcohols Using a Recyclable Polymer-Supported Isothiourea Catalyst in Batch and Flow
Neyyappadath, Rifahath Mon,Chisholm, Ross,Greenhalgh, Mark D.,Rodríguez-Escrich, Carles,Pericàs, Miquel A.,H?hner, Georg,Smith, Andrew D.
, p. 1067 - 1075 (2018/02/14)
A polystyrene-supported isothiourea catalyst, based on the homogeneous catalyst HyperBTM, has been prepared and used for the acylative kinetic resolution of secondary alcohols. A wide range of alcohols, including benzylic, allylic, and propargylic alcohols, cycloalkanol derivatives, and a 1,2-diol, has been resolved using either propionic or isobutyric anhydride with good to excellent selectivity factors obtained (28 examples, s values up to 600). The catalyst can be recovered and reused by a simple filtration and washing sequence, with no special precautions needed. The recyclability of the catalyst was demonstrated (15 cycles) with no significant loss in either activity or selectivity. The recyclable catalyst was also used for the sequential resolution of 10 different alcohols using different anhydrides with no cross-contamination between cycles. Finally, successful application in a continuous flow process demonstrated the first example of an immobilized Lewis base catalyst used for the kinetic resolution of alcohols in flow.
Ultrasound-assisted regioselective ring opening of epoxides with nitrogen heterocycles using pyrrolidonium and imidazolium-based acidic ionic liquids
Zakeri, Masoumeh,Nasef, Mohamed Mahmoud,Abouzari-Lotf, Ebrahim,Haghi, Hoda
, p. 10097 - 10108 (2016/01/12)
Imidazolium and N-methyl-2-pyrrolidonium ionic liquids under ultrasound irradiation were developed as a green and expeditious approach for C-alkylation and N-alkylation of the nitrogen heterocycles including indoles and imidazoles with aliphatic and aroma
An efficient Friedel-Crafts alkylation of nitrogen heterocycles catalyzed by antimony trichloride/montmorillonite K-10
Liu, Yu-Heng,Liu, Qiu-Shuang,Zhang, Zhan-Hui
scheme or table, p. 916 - 921 (2009/05/27)
It has been found that SbCl3 supported on montmorillonite K-10 is an efficient and reusable catalyst for Friedel-Crafts alkylation of nitrogen heterocycles such as indoles and pyrroles with epoxides. The reaction gives the corresponding C-alkyl
Homobenzotetramisole: An effective catalyst for kinetic resolution of aryl-cycloalkanols
Birman, Vladimir B.,Li, Ximin
supporting information; experimental part, p. 1115 - 1118 (2009/04/07)
Homobenzotetramisole (HBTM), a ring-expanded analogue of the previously reported catalyst BTM, displays higher catalytic activity and a different structure-selectivity profile. It displays good enantioselectivities in kinetic resolution of secondary benzylic alcohols but is particularly effective for 2-aryl-substituted cycloalkanols.
A simple, highly regioselective and efficient reaction of indole with epoxides under solvent-free conditions
Azizi, Najmedin,Mehrazma, Shokopheh,Saidi, Mohammad R.
, p. 800 - 803 (2007/10/03)
Lithium perchlorate has been found to be an inexpensive and efficient catalyst for the ring opening of epoxides by indole and N-methylindole, which provides an environmentally friendly method for the synthesis of substituted indoles. A complete regioselec
A versatile synthetic methodology for the synthesis of tryptophols
Garden, Simon J,Da Silva, Rosangela B,Pinto, Angelo C
, p. 8399 - 8412 (2007/10/03)
Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol.
Stereocontrolled syntheses of some conformationally restricted analogs of serotonin
Ghosh, Arun,Wang, Wuyi,Freeman, Jeremiah P.,Althaust, John S.,VonVoigtlander, Philip F.,Scahill, Terrence A.,Mizsak, Stephen A.,Szmuszkovicz, Jacob
, p. 8653 - 8662 (2007/10/02)
Syntheses of serotonin analogs 2 and 3 are described including a case of retention in the Mitsunobu reaction. An unusual stereoselectivity in a reductive animation sequence is also described. Dopamine and serotonin activity of the eight analogs has been d
