21777-32-2Relevant academic research and scientific papers
When ethyl is infinitely different from methyl: Double addition of lithiated dithianes to aromatic carboxylates revisited
Valiulin, Roman A.,Kottani, Rudresha,Kutateladze, Andrei G.
, p. 5047 - 5049 (2006)
Addition of lithiated alkyl dithianes to benzoyl chloride or methyl benzoate does not produce the expected product of double addition, α,α-bis(alkyldithianyl) benzyl alcohol, for alkyls larger than methyl. Instead, the first step intermediate, i.e. 2-benz
An alternative stereoselective total synthesis of Verbalactone
Vanjivaka, Sreelatha,Ramanakumar, Kakarla,Rajeswari,Vantikommu, Jyothi,Sridhar, Gattu,Palle, Sadanandam
, p. 50 - 57 (2018)
A simple and efficient synthesis of Verbalactone has been accomplished from inexpensive and commercially available starting material, hexanal. This concise synthesis utilizes stereoselective reduction of β-hydroxyketone using catecholborane, regioselective opening of epoxide and Yamaguchi reaction for the construction of the macrolactone.
Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions
Deng, Xingwang,Zhou, Guan,Tian, Jing,Srinivasan, Rajavel
supporting information, p. 7024 - 7029 (2020/12/29)
We report the facile amide-forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high-yielding and displays excellent functional-group tolerance. Late-stage modifications of an array of marketed drugs, peptides, natural products, and biologically active compounds showcase the robustness and functional-group tolerance of the reaction. The key to the success of the reaction could be the possible formation of the strong Si?O bond via a Brook-type rearrangement. Given its simplicity and efficiency, this ligation has the potential to unfold new applications in the areas of medicinal chemistry and chemical biology.
A 2 - substituted - 1, 3 - dithiane derivative of the preparation method
-
Paragraph 0023; 0024; 0025; 0026; 0028, (2019/06/26)
The invention provides a preparation method of a 2-substituted-1,3-dithiane derivative. The preparation method comprises the following steps: adding 1,3-dithiane (CAS:505-23-7) and 1,2-dichloroethane (DCE) or dichloromethane (DCM) into a reaction bottle, adding N-chlorosuccinimide (NCS) under ice-bath condition, and stirring for 0.5-1 h to prepare a 2-chloro-1,3-dithiane solution; and adding an aldehyde or ketone compound and a lewis acid catalyst into the above solution, and reacting to prepare the 2-substituted-1,3-dithiane derivative. By using the 1,3-dithiane solid and different types of aldehyde and keto-carbonyl compounds as raw material and using one or more of ferric trichloride, boron trifluoride diethyl etherate, methanesulfonic acid, aluminum trichloride, ferrous chloride and nickel chloride as catalysts, preparation of the 2-substituted-1,3-dithiane derivative is realized. The catalysts used in the invention are cheap and easily available, dosage of the catalysts is low and pollution of the catalysts is little. The solid raw materials used in the invention can avoid use of fetid toxic 1,3-dimercaptopropane with strong volatility, and the purpose of protecting an experimenter's body and reducing environmental pollution is realized. In addition, the preparation method has advantages of mild reaction condition, high yield, simple operation and the like.
Pot-economy autooxidative condensation of 2-Aryl-2-lithio-1,3-dithianes
Vale, Joao R.,Rimpil?inen, Tatu,Siev?nen, Elina,Rissanen, Kari,Afonso, Carlos A. M.,Candeias, Nuno R.
, p. 1948 - 1958 (2018/02/23)
The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.
Re2O7-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles
Sittiwong, Wantanee,Richardson, Michael W.,Schiaffo, Charles E.,Fisher, Thomas J.,Dussault, Patrick H.
supporting information, p. 1526 - 1532 (2013/10/22)
Re(VII) oxides catalyze the acetalization, monoperoxyacetalization, monothioacetalization and allylation of hemiacetals. The reactions, which take place under mild conditions and at low catalyst loadings, can be conducted using hemiacetals, the corresponding O-silyl ethers, and, in some cases, the acetal dimers. Aldehydes react under similar conditions to furnish good yields of dithioacetals. Reactions of hemiacetals with nitrogen nucleophiles are unsuccessful. 1,2-Dioxolan-3-ols (peroxyhemiacetals) undergo Re(VII)-promoted etherification but not allylation. Hydroperoxyacetals (1-alkoxyhydroperoxides) undergo selective exchange of the alkoxide group in the presence of either Re2O7 or a Bronsted acid.
Preyssler-type heteropoly acid: A new, mild and efficient catalyst for protection of carbonyl compounds
Rahimizadeh, Mohammad,Bazazan, Tahmineh,Shiri, Ali,Bakavoli, Mehdi,Hassani, Hassan
experimental part, p. 435 - 438 (2012/01/03)
Preyssler-type heteropoly acid is introduced as a new, mild and efficient catalyst for protection of a variety of carbonyl compounds with 1,3-propane dithiol.
Chemoselective dithioacetalization of carbonyl compounds using magnesium hydrogensulfate as efficient heterogeneous catalyst
Shaterian, Hamid Reza,Hosseinian, Asghar,Ghashang, Majid,Khorami, Fahimeh
experimental part, p. 2490 - 2501 (2009/08/07)
Carbonyl compounds have been successfully converted into their corresponding dithiolanes and dithianes derivatives with 1,2-ethanedithiol and 1,3-propanedithiol in excellent yield at room temperature and short reaction times using a catalytic amount of ma
2,4,6-Trichloro-1,3,5-triazine catalyzed chemoselective transthioacetalization of aldehyde acetals and oxathioacetals
Bandgar, Babasaheb P.,Joshi, Neeta S.,Bettigeri, Sampada V.
, p. 67 - 71 (2007/10/03)
A mild and efficient transthioacetalization of aldehyde acetals and oxathioacetals was carried out using 2,4,6-trichloro-1,3,5-triazine as a mild and inexpensive catalyst. Chemoselective transacetalization is impressive as aldehyde O,O- and O,S-acetals ar
A mild and chemoselective dithioacetalization of aldehydes in the presence of anhydrous copper (II) sulfate
Moghaddam, Firouz Matloubi,Bardajee, Ghasem Rezanejade,Oskui, Afsane Arefi
, p. 1445 - 1450 (2007/10/03)
Various aldehydes have been protected with different thiols as dithioacetals with excellent yields using anhydrous copper sulfate as a mild and chemoselective catalyst. The reaction is carried out in a solvent and/or under solvent-free conditions. The transthioacetalization of oxyacetals into dithioacetals was also achieved in an excellent yield. Copyright Taylor & Francis Group, LLC.
