71700-50-0Relevant academic research and scientific papers
Oxidative Cleavage of Silyl Ethers by an Oxoammonium Salt
Loman, Jacob J.,Pistritto, Vincent A.,Kelly, Christopher B.,Leadbeater, Nicholas E.
, p. 2372 - 2377 (2016/09/28)
A method for the oxidative cleavage of silyl ethers to their corresponding carbonyl species mediated by an oxoammonium salt is described. The resulting aldehydes and ketones are obtained under mild reaction conditions with no observed overoxidation. For robust substrates, heating to reflux temperatures significantly reduces the reaction time.
Lewis acid-promoted electron transfer deoxygenation of epoxides, sulfoxides, and amine N-oxides: the role of low-valent niobium complexes from NbCl5 and Zn
Oh, Kyungsoo,Knabe, William Eric
experimental part, p. 2966 - 2974 (2009/05/30)
A mild and operationally simple deoxygenation of epoxides, sulfoxides, and amine N-oxides is described using a sub-stoichiometric amount of low-valent niobium complexes generated in situ from commercially available NbCl5 and zinc dust. The deoxygenation proceeds by a reductive cleavage of polarized O-C/O-N/O-S bonds through a single electron transfer from zinc metal to the niobium-substrate complex due to the high oxophilic nature of the niobium species. The presence of adjacent radical-stabilizing groups is beneficial to epoxide substrates; however the similar prerequisite does not apply to sulfoxides and amine N-oxides, where a broad range of substrates are efficiently deoxygenated in excellent yields.
Facile and convenient method of deuterium gas generation using a Pd/C-catalyzed H2-D2 exchange reaction and itsapplication to synthesis of deuterium-labeled compounds
Kurita, Takanori,Aoki, Fumiyo,Mizumoto, Takuto,Maejima, Toshihide,Esaki, Hiroyoshi,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
supporting information; experimental part, p. 3371 - 3379 (2009/04/10)
The Pd/C-catalyzed H2-D2 exchange reaction using a H2-D2O combination provided a general, efficient and environmentally friendly route for the preparation of deuterium gas (D 2). H2 sealed
Kinetic Resolution of Epoxides by a C-C Bond-Forming Reaction: Highly Enantioselective Addition of Indoles to cis, trans, and meso Aromatic Epoxides Catalyzed by [Cr(salen)] Complexes
Bandini, Marco,Cozzi, Pier Giorgio,Melchiorre, Paolo,Umani-Ronchi, Achille
, p. 84 - 87 (2007/10/03)
The high reactivity of indoles has led to a new approach for the kinetic resolution of epoxides. [Cr(salen)] efficiently catalyzes a new C-C bond-forming reaction that allows the kinetic resolution of cis and trans aromatic epoxides (see scheme). By employing the same catalytic system, different indolyl derivatives were obtained in high enantiomeric excesses (up to 98%) by asymmetric ring opening of meso-stilbene oxide.
An Effective Approach for the Silylation of Hydroxyl Compounds in Room Temperature Ionic Liquids
Xu, Zhen-Yuan,Xu, Dan-Qian,Liu, Bao-You,Luo, Shu-Ping
, p. 4143 - 4149 (2007/10/03)
The room temperature ionic liquid (RTIL) 1-n-butyl-3-methylimidazolium hexafluorophosphate (BMImPF6) is used as a "green" recyclable alternative to conventional solvents for the silylation of a series of hydroxyl compounds (alcohols and phenols
A Convenient Method for Protection and Deprotection of Alcohols and Phenols as Alkylsilyl Ethers Catalyzed by Iodine under Microwave Irradiation
Saxena, Ira,Deka, Nabajyoti,Sarma, Jadab C.,Tsuboi, Sadao
, p. 4185 - 4191 (2007/10/03)
Irradiation of alcohols or phenols with tert-butyldimethylsilyl chloride (TBDMSCl) or trimethylsilyl chloride (TMSCl) in presence of catalytic amount (20 mol%) of iodine in a microwave oven for 2 min gives the corresponding silyl ethers in excellent yield. Iodine in methanol deprotects the silyl ether into its parent alcohol or phenol under similar reaction conditions.
Nonionic superbase-catalyzed silylation of alcohols
D'Sa, Bosco A.,McLeod, Dale,Verkade, John G.
, p. 5057 - 5061 (2007/10/03)
Herein we report a very effective and mild procedure for the silyl protection of a wide variety of substrate alcohols, including primary, secondary, allylic, propargylic, benzylic, hindered secondary, tertiary, acid-sensitive, and base-sensitive alcohols and also hindered phenols. The silylation reagent used is tert-butyldimethylsilyl chloride (TBDMSCl) and the catalyst is P(MeNCH2CH2)3N, 1b, both of which are commercially available. The reactions are carried out in acetonitrile from 24 to 40 °C and on rare occasions in DMF from 24 to 80 °C. The effect of solvent, catalyst concentration, and temperature and reaction time on the silylation of alcohols and the excellent compatibility of our method with a variety of functional groups is discussed. An efficient method for recycling the catalyst is also presented. Although representative primary alcohols, secondary alcohols, and phenols were silylated using the more sterically hindered reagent tert-butyldiphenylsilyl chloride (TBDPSCl) in the presence of lb as a catalyst, tertiary alcohols were recovered unchanged.
Studies of Regio- and Stereoselectivity in Some Nucleophilic Ring Opening Reactions of N-Tosyl-3-phenyl-2-aziridinemethanols and Derivatives
Tanner, David,Gautun, Odd R.
, p. 8279 - 8288 (2007/10/02)
A study has been made of the regio- and stereoselectivity of the ring opening reactions of the 3-aryl substituted aziridines 1 and 2.The regiochemical outcome is apparently decided by a balance of electronic activation at C-3 by the phenyl group and the c
Enantioselective synthesis of goniobutenolides A and B
Ko, Soo Y.,Lerpiniere, Joanne
, p. 2101 - 2104 (2007/10/02)
Goniobutenolides A and B were synthesized in the enantiopure forms, employing the asymmetric dihydroxylation and cyclic sulfate rearrangement-opening reactions as the key stereocenter-forming steps.
An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction
Ko, Soo Y.,Malik, Majbeen,Dickinson, A. Frances
, p. 2570 - 2576 (2007/10/02)
A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction.Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate.Upon desilylation, this compound undergoes a Payne-type rearrangement.Nucleophilic epoxide-opening then provides an erythro-2,3-diol.The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel.Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures.Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, -N3, -OAc, -CN, halides as well as carbon nucleophiles and hydride.
