62791-22-4Relevant academic research and scientific papers
Sulfoniosilylation of α,β-Unsaturated Carbonyl Compounds. Facile Nucleophilic Substitution of 3-Trialkylsilyloxyalk-2-enylenesufonium Salts
Kim, Sunggak,Park, Joo Hyeon,Kim, Yong Gil,Lee, Joo Moon
, p. 1188 - 1189 (1993)
Sulfoniosilylation of α,β-enones and α,β-enals with trialkylsilyl triflate and dimethyl sulfide at -78 deg C affords 3-trialkylsilyloxyalk-2-enylenesulfonium salts, which undergo facile nucleophilic substitution with various nucleophiles.
Chiral Zinc(II)-Catalyzed Enantioselective Tandem α-Alkenyl Addition/Proton Shift Reaction of Silyl Enol Ethers with Ketimines
Kang, Tengfei,Cao, Weidi,Hou, Liuzhen,Tang, Qiong,Zou, Sijia,Liu, Xiaohua,Feng, Xiaoming
, p. 2464 - 2468 (2019)
A new catalytic asymmetric tandem α-alkenyl addition/proton shift reaction of silyl enol ethers with ketimines was serendipitously discovered in the presence of chiral N,N′-dioxide/ZnII complexes. The proton shift preferentially proceeded inste
Copper-Catalyzed Formal Dehydrogenative Coupling of Carbonyls with Polyfluoroarenes Leading to β-C-H Arylation
Xie, Weilong,Kim, Dongwook,Chang, Sukbok
supporting information, p. 20588 - 20593 (2020/12/23)
We herein communicate a formal dehydrogenative coupling of carbonyls with polyfluoroarenes enabled by Cu catalysis. Silyl enol ethers initially prepared from carbonyls are postulated to undergo the copper-mediated oxidative dehydrogenative coupling with polyfluoroarenes via a radical pathway. Including cyclic and linear ketones, aldehydes, and esters, a broad range of β-aryl carbonyl products were efficiently obtained in high regio- and stereoselectivity with excellent functional group tolerance.
Synthesis of Functionalized Medium-Sized trans-Cycloalkenes by 4π Electrocyclic Ring Opening/Alkylation Sequence
Ito, Tomohiro,Tsutsumi, Masaki,Yamada, Ken-ichi,Takikawa, Hiroshi,Yamaoka, Yousuke,Takasu, Kiyosei
supporting information, p. 11836 - 11840 (2019/07/31)
Development of a novel synthetic method for medium-sized trans-cycloalkenes (TCAs) is described. Functionalized TCAs are readily prepared from simple cycloalkanones in a few steps, namely, enol silyl ether formation, [2+2] cycloaddition, and domino 4π ele
One-Pot Synthesis of Silylated Enol Triflates from Silyl Enol Ethers for Cyclohexynes and 1,2-Cyclohexadienes
Inoue, Kazuki,Nakura, Ryo,Okano, Kentaro,Mori, Atsunori
supporting information, p. 3343 - 3347 (2018/07/13)
Regiocontrolled synthesis of precursors for strained cyclohexynes and 1,2-cyclohexadienes is described based on one-pot rearrangement of silyl enol ether followed by formation of enol triflate. Treatment of silyl enol ether with a combination of LDA and tBuOK led to the migration of the silyl group to generate α-silyl enolate, which was treated with Comins' reagent to provide the corresponding enol triflate. The transient α-silylated lithium enolate was smoothly isomerized in the presence of stoichiometric amount of water within one hour at room temperature, providing precursors for cyclohexynes exclusively in one pot. Effects of silyl groups, isomerization of the lithium enolate, and regiocontrolled generation of these precursors for these strained molecules were also investigated.
Unprecedented alkylation of silicon enolates with alcohols via carbenium ion formations catalyzed by tin hydroxide-embedded montmorillonite
Tandiary, Michael Andreas,Asano, Masashi,Hattori, Taiki,Takehira, Satoshi,Masui, Yoichi,Onaka, Makoto
supporting information, p. 1925 - 1928 (2017/04/27)
The solid acid, tin hydroxide-embedded montmorillonite, catalyzes the unprecedented alkylation of various silicon enolates with primary, secondary and tertiary benzylic alcohols as well as secondary allylic alcohols. The acid catalysis of Sn-Mont was not only higher than that of the other ion-exchanged montmorillonites (M-Mont; M?=?H, Ti, Fe and Al), but also higher than that of the typical homogeneous acid catalysts such as BF3·OEt2, TMSOTf and TfOH.
The synthesis of pyrroles and oxazoles based on gold α-imino carbene complexes
Loy, Nicole S. Y.,Choi, Subin,Kim, Sunggak,Park, Cheol-Min
supporting information, p. 7336 - 7339 (2016/06/14)
Cationic gold complexes of α-oximimino carbenes have been identified to react with weak nucleophiles including enol ethers and nitriles. These findings allowed us to develop the highly efficient synthesis of pyrroles and oxazoles.
Synthesis of α,β-unsaturated carbonyl compounds via a visible-light-promoted organocatalytic aerobic oxidation
Zhang, Junlin,Wang, Leming,Liu, Qi,Yang, Zhen,Huang, Yong
supporting information, p. 11662 - 11664 (2013/12/04)
α,β-Unsaturated ketones and aldehydes have been synthesized from their corresponding silyl enol ethers in a straightforward protocol involving a visible-light promoted organocatalytic, aerobic oxidation reaction. A cheap organic dye was used catalytically in these reactions as the photosensitizer.
METHOD FOR PRODUCING SILYLENOL ETHERS
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Paragraph 0105, (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.
The introduction of a double bond on the steroid skeleton - The preparation of enol silyl ether derivatives from vicinal diols
Marek, Ales,Klepetarova, Blanka,Elbert, Tomas
experimental part, p. 443 - 456 (2011/12/21)
The ways of converting steroid vicinal diol into an unsaturated derivative were studied with the intention of preparing suitable precursors for the introduction of deuterium or tritium into the molecules of brassinosteroids. The model vicinal diol compound, 2α,3α-dihydroxy-5α-pregnane-6, 20-dione (3), was converted with high regioselectivity to the α-hydroxy ketone derivative, 2α-hydroxy-5α-pregnane-3,6,20-trione (8), in a 75% yield. The attempts to convert α-hydroxy ketone 8 to the dioxolene derivative, 2α,3α-(isopropylidenedioxy)-5α-pregn-2-ene-6,20- dione (6), failed. The conditions for the conversion of ketone to the corresponding enol trialkylsilyl ether were optimized using cyclohexanone as a model compound. The best and reproducible results were obtained by using tert-butyldimethylsilyl trifluoromethansulfonate (TBDMSiOTf) as the silylating reagent and triethylamine as the base. Under these conditions, the 3,6,20-trione (8) was converted to 2,3-bis(tert-butyldimethylsilyloxy)-5α-pregn-2-ene- 6,20-dione (14) with a 66% yield.
