133576-46-2Relevant academic research and scientific papers
Diastereoselective synthesis of β-hydroxy sulfoxides: Enzymatic and biomimetic approaches
Colonna, Stefano,Pironti, Vincenza,Zambianchi, Francesca,Ottolina, Gianluca,Gaggero, Nicoletta,Celentano, Giuseppe
, p. 363 - 368 (2007)
Stereoselectivities of up to 98 % have been found in the enzymatic synthesis of β-hydroxy sulfoxides catalyzed by cyclohexanone monooxygenase (CHMO). The diastereoselectivity of the "one-pot" preparation of the title compounds in the presence of bovine se
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.
Biodegradable choline hydroxide promoted environmentally benign thiolysis of epoxides
Azizi, Najmedin,Edrisi, Mahtab
supporting information, p. 525 - 528 (2016/01/20)
An environmentally benign and rapid thiolysis of epoxides using a biodegradable, choline-based task-specific ionic liquid has been developed. The ring opening reaction of aryl and alkyl epoxides proceeded rapidly and afforded the corresponding β-hydroxysulfides in high yields with excellent regioselectivity. The protocol has the advantages of easy work-up, short reaction times, high yields, and a biodegradable catalyst.
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,
LiOH-catalyzed simple ring opening of epoxides under solvent-free conditions
Azizi, Najmedin,Khajeh-Amiri, Alireza,Ghafuri, Hossein,Bolourtchian, Mohammad
scheme or table, p. 1550 - 1557 (2010/09/06)
LiOH has been found to be a very simple and selective catalyst for the rapid and mild synthesis of β-hydroxy sulfides and β-hydroxyl nitriles by ring opening of epoxides with aromatic, aliphatic, and heterocyclic thiols and trimethylsilyl cyanide at room temperature under solvent free conditions. All the reactions proceeded satisfactorily in short times and afforded the corresponding products in good to excellent yields with high regioselectivity and chemoselectivity under mild reaction conditions. Copyright Taylor & Francis Group, LLC.
One-pot synthesis of β-amino/β-hydroxy selenides and sulfides from aziridines and epoxides
Ganesh, Venkataraman,Chandrasekaran, Srinivasan
experimental part, p. 3267 - 3278 (2010/02/27)
Diaryl disulfides and diselenides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate the corresponding thiolate and selenolate species in situ, which effect the ring opening of aziridines and epoxides in a reg
Catalytic asymmetric ring-opening reaction of meso-epoxides with aryl selenols and thiols catalyzed by a heterobimetallic gallium-titanium-salen complex
Sun, Jiangtao,Yang, Minghua,Yuan, Fang,Jia, Xuefeng,Yang, Xia,Pan, Yi,Zhu, Chengjian
supporting information; experimental part, p. 920 - 930 (2009/11/30)
A chiral heterobimetallic Lewis acid complex has been developed as an efficient catalyst. The enantioselective desymmetrization of meso-epoxides with aryl selenols and thiols catalyzed by the heterobimetallic complex has been optimized. The optically active β-arylseleno alcohols and β-hydroxy sulfides were obtained in good yields and high enantioselec- tivities (up to 97% ee and 92% ee, respectively). A strong synergistic effect between different Lewis acids was exhibited in the catalytic process. & copy; 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
