19980-33-7Relevant academic research and scientific papers
Mixed alkylamido aluminate as a kinetically controlled base
Naka, Hiroshi,Morey, James V.,Haywood, Joanna,Eisler, Dana J.,McPartlin, Mary,Garcia, Felipe,Kudo, Hironaga,Kondo, Yoshinori,Uchiyama, Masanobu,Wheatley, Andrew E. H.
, p. 16193 - 16200 (2008)
The mechanisms by which directed ortho metalation (DoM) and postmetalation processes occur when aromatic compounds are treated with mixed alkylamido aluminate i-Bu3Al(TMP)Li (TMP-aluminate 1; TMP = 2,2,6,6- tetramethylpiperidide) have been inve
METHOD FOR PRODUCING SILYLENOL ETHERS
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Paragraph 0098; 0103, (2013/03/26)
The present invention provides a method for producing a silyl enol ether compound, which is convenient, has highly broad utility and places a low environmental load (less waste). The present invention relates to a method for producing silyl enol ether compound (3), including reacting ketone or aldehyde compound (1) with allylsilane compound (2) in the presence of a base and 0.00001 to 0.5 equivalents of an acid catalyst relative to ketone or aldehyde compound (1), wherein R1 is a hydrogen atom, an alkyl group, an aryl group or the like; R2 and R3 are each a hydrogen atom, a halogen atom, an alkyl group, an aryl group or the like; R1 and R3, R1 and R2, or R2 and R3 optionally form a ring, together with the carbon atom(s) bonded thereto; R4 , R5 and R6 are each a hydrogen atom, an alkyl group or the like; two of R4, R5 and R6 optionally form a ring; R7, R8, R9, R10 and R11 are each a hydrogen atom, an alkyl group or the like; two of R7, R8, R9, R10 and R11 optionally form a ring.
Efficient control for the cationic platinum(II)-catalyzed concise synthesis of two types of fused carbocycles with angular oxygen functionality
Kusama, Hiroyuki,Watanabe, Eiichi,Ishida, Kento,Iwasawa, Nobuharu
supporting information; experimental part, p. 2273 - 2277 (2012/06/30)
Double trouble: An efficient method for the preparation of two types of synthetically useful bicyclo[5.4.0]undecanes with an angular oxygen functionality was realized starting from easily available substrates; this method was based on the [3+2] cycloaddit
Mechanistic studies on α-trifluoromethylation of ketones via silyl enol ethers and its application to other carbonyl compounds
Sato, Kazuyuki,Yuki, Takashi,Yamaguchi, Ryoji,Hamano, Tetsuya,Tarui, Atsushi,Omote, Masaaki,Kumadaki, Itsumaro,Ando, Akira
supporting information; experimental part, p. 3815 - 3819 (2009/10/01)
(Chemical Equation Presented) Synthesis of α-CF3 carbonyl compounds has been recognized to be difficult up to now because the polarization of CF3δ--Iδ+ is opposite to that of CH3δ+-Iδ-, and this makes it difficult to introduce CF3+ unit to enolates. We recently reported an effective R-trifluoromethylation of ketones by using Et 2Zn with Rh catalyst, but the mechanism has not fully been cleared. Now, we carried out the detailed mechanistic studies and found the involvement of a highly reactive alkylrhodium complex which derived from Et2Zn and RhCl(PPh3)3 in this α-trifluoromethylation. Furthermore, this α-trifluoromethylation was applied to other types of carbonyl compounds in good yields.
CuBr-catalyzed reaction of N,N-dimethylanilines and silyl enol ethers: An alternative route to β-arylamino ketones
Huang, Lehao,Zhang, Xunbin,Zhang, Yuhong
supporting information; experimental part, p. 3730 - 3733 (2011/03/18)
Image Presented A wide range of silyl enol ethers undergo the reactions with N,N-dimethylanilines in the presence of transition metal catalysts under mild conditions to give β-arylamino ketones. In the cases of silyl enol ethers derived from unsymmetrical ketones, regiospecific addition of carbonyl compounds was obtained at the olefinic position of silyl enol ether.
In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers
Kerr, William J.,Watson, Allan J. B.,Hayes, Douglas
experimental part, p. 1238 - 1243 (2008/10/09)
Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes2Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high yielding one-pot process. The Royal Society of Chemistry.
Di-tert-butylmagnesium as an atom-efficient, carbon-centred base reagent for the preparation of silyl enol ethers from ketones
Kerr, William J.,Watson, Allan J. B.,Hayes, Douglas
experimental part, p. 1386 - 1390 (2009/04/06)
Di-tert-butylmagnesium has been found to be a reactive, yet non-nucleophilic and non-reductive, carbon-centred base for the deprotonation of a series of ketones. This reagent demonstrates equally high reactivity when used as either the pre-formed reagent, or in a more accessible one-pot protocol from the parent Grignard reagent, and offers improved atom-efficiency over more traditionally employed bases. Georg Thieme Verlag Stuttgart.
Chiral and achiral lithium amides having a fluorous ponytail: Preparation and evaluation as a recycling reagent for lithium enolate generation
Matsubara, Hiroshi,Maeda, Louis,Sugiyama, Hiroyuki,Ryu, Ilhyong
, p. 2901 - 2912 (2008/03/13)
Diisopropylamine derivatives bearing a perfluoroalkyl chain were prepared and converted to the corresponding lithium amides by treatment with n-butyllithium. The fluorous lithium amides reacted with ketones to efficiently produce lithium enolates. Asymmetric deprotonation of prochiral ketones was also studied using lithium amides derived from chiral fluorous amines, which gave optical yields comparable with the parent nonfluorous chiral lithium amides. These reusable fluorous amines can be easily recovered by liquid-liquid extraction or chromatographic separation. Georg Thieme Verlag Stuttgart.
Bismesitylmagnesium: A thermally stable and non-nucleophilic carbon-centred base reagent for the efficient preparation of silyl enol ethers
Kerr, William J.,Watson, Allan J. B.,Hayes, Douglas
, p. 5049 - 5051 (2008/09/17)
Bismesitylmagnesium has been established as an accessible, practical, convenient, and non-nucleophilic carbon-centred base reagent for efficient access to silyl enol ethers from a series of ketone substrates at readily utilisable temperatures. The Royal Society of Chemistry.
The enantioselective Tsuji allylation
Behenna, Douglas C.,Stoltz, Brian M.
, p. 15044 - 15045 (2007/10/03)
The first catalytic enantioselective examples of the Tsuji allylation using enol carbonates and enol silanes are described. The products possess a quaternary stereogenic center and are useful building blocks for synthetic chemistry. Copyright
