102917-46-4Relevant academic research and scientific papers
Stereoselective Synthesis of a Bicyclic Ketooxetane via a Thionium Ion-Mediated Cyclisation Reaction
Craig, Donald,Lawrence, Ronnie M.,Tapolczay, David J.
, p. 1001 - 1003 (1997)
The synthesis of a bicyelic ketooxetane using as the key step the ethylaluminium dichloride-mediated cyclisation of a Z-silyl enol ether onto a thionium ion 'trigger' attached to a five-membered carbocyclic template is described. Attempted cyclisation of the analogous substrate possessing a six-membered ring did not afford the oxetane, but instead the product of 1,2-hydride shift. The mechanism of this unexpected transformation was conclusively established by analysis of the products of attempted cyclisation of a deuterium-labelled substrate.
Facile room-temperature MgBr2·OEt2-catalyzed thiolysis of epoxides under solvent-free conditions
Mojtahedi, Mohammad M.,Abaee, M. Saeed,Bolourtchian, Mohammad,Abbasi, Hassan
, p. 905 - 910 (2007)
Solvent-free ring opening of 1,2-epoxides with aromatic and aliphatic thiols under 1 mol% magnesium bromide ethyl etherate catalysis affords rapid formation of β-hydroxy sulfides at ambient temperature with excellent yields. Nucleophilic attack of the thi
Fluoro alcohol as reaction medium: One-pot synthesis of β-hydroxy sulfoxides from epoxides
Kesavan, Venkitasamy,Bonnet-Delpon, Danièle,Bégué, Jean-Pierre
, p. 2895 - 2898 (2000)
β-Hydroxy sulfoxides were obtained in one-pot synthesis by the ring opening of oxiranes with thiols in hexafluoroisopropanol (HFIP) without any catalyst, followed by in situ oxidation under neutral conditions. The reaction is anti-selective. β-Hydroxy sulfoxides were transformed by pyrolysis in the corresponding allylic alcohols. (C) 2000 Elsevier Science Ltd.
Regioselective ring opening of epoxides by nucleophiles mediated by lithium bistrifluoromethanesulfonimide
Cossy, Janine,Bellosta, Véronique,Hamoir, Claire,Desmurs, Jean-Roger
, p. 7083 - 7086 (2002)
In the presence of LiNTf2, epoxides undergo ring opening with high regioselectivity and in good yield when they are treated with nucleophiles such as amines, hydrazines and thiophenol.
Synthesis and application of Cu(II) immobilized MCM-41 based solid Lewis acid catalyst for aminolysis reaction under solvent-free condition
Chaudhary, Garima,Gupta, Neha,Singh, Amit Pratap
, (2021/07/22)
In this paper, a Cu(II) immobilized periodic mesoporous organosilica (PMOs) was synthesized and used as a reusable solid Lewis acid catalyst for the aminolysis of epoxides under solvent-free conditions. An amide-based ligand, L-propylsilyl (1) having a specific binding pocket was prepared and fabricated on mesoporous MCM-41 to produce mesoporous organosilica L-propylsilyl@MCM-41 (2). Further, it has been utilized for anchoring Cu(II) ions under controlled reaction conditions to yield solid Lewis acid catalyst Cu(II)-L-propylsilyl@MCM-41 (3). The synthesized catalyst 3 exhibits significantly higher catalytic activity for aminolysis compared to hitherto known solid Lewis acid catalysts. An extensive range of β-amino alcohols with high regio and stereoselectivity were prepared by using catalyst 3. The catalyst was recovered easily and reused eight times without any loss in its catalytic activity. Furthermore, the synthesis of clinically significant propranolol (β-blocker) from α- naphthyl glycidyl ether was attained successfully using catalyst 3 in a very decent yield.
Lithium BINOL phosphate catalyzed desymmetrization of meso-epoxides with aromatic thiols
Ingle, Gajendrasingh,Mormino, Michael G.,Antilla, Jon C.
supporting information, p. 5548 - 5551 (2015/02/19)
A highly enantioselective method for desymmetrization of meso-epoxides using thiols is reported. This is the first example of epoxide activation achieved using metal BINOL phosphates. The reaction has a broad scope in terms of epoxide substrates and aroma
Rapid, benign, and additive-free thiolysis of epoxides under ultrasonic/aqueous conditions
Mojtahedi, Mohammad M.,Khalili, Sajad
, p. 431 - 437 (2014/06/10)
An environmentally friendly and efficient procedure is developed for ring opening of various epoxides with thiols under non-thermal conditions. Reactions take place by ultrasonic irradiation of the two reactants suspended in an additive-free aqueous mediu
Highly enantioselective kinetic resolution of trans-2-(phenylthio) cyclohexanol derivatives by immobilized Candida antartica B lipase
Chimni, Swapandeep Singh,Kaur, Kirandeep,Bala, Neeraj
, p. 67 - 74 (2013/10/22)
Candida antartica B (immobilized CAL-B) mediated resolutions of trans-2-(phenylthio)cyclohexanol derivatives using vinyl acetate as acylating agent and MTBE as solvent provide excellent enantioselectivity (up to >99%) and high yield of both the enantiomer
Recyclable superparamagnetic Fe3O4 nanoparticles for efficient catalysis of thiolysis of epoxides
Mojtahedi, Mohammad M.,Abaee, M. Saeed,Rajabi, Azam,Mahmoodi, Peyman,Bagherpoor, Saeed
experimental part, p. 68 - 71 (2012/08/07)
An efficient and rapid procedure is developed for room-temperature ring opening of various epoxides with thiols under solvent-free conditions in the presence of catalytic amount of superparamagnetic Fe3O4 nanoparticles. As a result,
Efficient synthesis of-Hydroxy sulfides and-Hydroxy sulfoxides catalyzed by Cu/MgO under solvent-free conditions
Das, Biswanath,Balasubramanyam, Penagaluri,Krishnaiah, Maddeboina,Veeranjaneyulu, Boyapati,Sudhakar, Dega
experimental part, p. 2113 - 2121 (2010/08/13)
Regio-, stereo-, and chemoselective ring opening of epoxides with thiols using Cu/MgO as a heterogeneous catalyst has efficiently been carried out to produce the corresponding β-hydroxy sulfides in excellent yields at room temperature under solvent-free c
