133690-98-9Relevant academic research and scientific papers
Regioselective access to CF3S-substituted dihydrofurans from homopropargylic alcohols with trifluoromethanesulfenamide
Chen, Dao-Qian,Gao, Pin,Zhou, Ping-Xin,Song, Xian-Rong,Qiu, Yi-Feng,Liu, Xue-Yuan,Liang, Yong-Min
, p. 6637 - 6639 (2015)
A facile access to 4-((trifluoromethyl)thio)-2,3-dihydrofurans from unprotected homopropargylic alcohols in high regioselectivity is reported. This method is the first example of using a free hydroxy group as a nucleophile to complete a trifluoromethylthiolation/cyclization protocol with an alkyne in moderate to excellent yields. This journal is
Stereodivergent Palladium- And Rhodium-Catalyzed Intramolecular Addition of Tosylureas to Allenes: Diastereoselective Synthesis of Tetrahydropyrimidinones
Breit, Bernhard,Geissler, Arne G. A.,Riesterer, Jasmin R.
supporting information, p. 9168 - 9172 (2021/12/06)
The intramolecular addition of tosylureas to allenes is highly syn-/anti-diastereoselective when employing a palladium or rhodium-based catalytic system and affords 1,3-cyclic ureas. Under palladium catalysis a range of thermodynamic anti-tetrahydropyrimi
One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping
Yamane, Daichi,Tanaka, Haruna,Hirata, Akihiro,Tamura, Yumiko,Takahashi, Daichi,Takahashi, Yusuke,Nagamitsu, Tohru,Ohtawa, Masaki
supporting information, p. 2831 - 2835 (2021/05/05)
A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.
Photoredox propargylation of aldehydes catalytic in titanium
Calogero, Francesco,Gualandi, Andrea,Di Matteo, Marco,Potenti, Simone,Fermi, Andrea,Bergamini, Giacomo,Cozzi, Pier Giorgio
, p. 7002 - 7009 (2021/05/29)
A practical and effective photoredox propargylation of aldehydes promoted by 10 mol % of [Cp2TiCl2] is presented. No stoichiometric metals or scavengers are used for the process. A catalytic amount of the cheap and simply prepared or
Silylcyclopropanes by Selective [1,4]-Wittig Rearrangement of 4-Silyl-5,6-dihydropyrans
Mori-Quiroz, Luis M.,Maloba, Emmanuel W.,Maleczka, Robert E.
supporting information, p. 5724 - 5728 (2021/07/31)
4-Silyl-5,6-dihydropyrans undergo remarkably selective [1,4]-Wittig rearrangements to give silylcyclopropanes in good yields. The selectivity is independent of the silyl group, but it is influenced by the electronic character of the migrating center. Elec
Synthesis of vinylic sulfones in aqueous media
Goh, Jeffrey,Maraswami, Manikantha,Loh, Teck-Peng
supporting information, p. 1060 - 1065 (2021/02/16)
A green method for the sulfination of allenic carbonyl compounds to access a wide variety of vinylic sulfones is developed. This reaction works in aqueous media under very mild conditions. This reaction is atom economic. A wide variety of vinylic sulfones could be obtained in moderate to excellent yields with wide functional group tolerance. The efficiency of this method is demonstrated in some reactions where the desired products can be isolated by filtration.
Formal metal-free γ-arylation of 1,3-dicarbonyl compounds: Via an isomerisation/1,4-addition/[3,3]-sigmatropic rearrangement sequence
Guan, Xi-Dong,Lu, Shi-Chao,Wen, Fu-Qiang
supporting information, p. 8964 - 8968 (2021/11/27)
A metal-free redox arylation of alkynes with sulfoxides has been developed to provide unconventional access to diverse γ-arylated 1,3-dicarbonyl compounds in an atom-economical manner. Mechanistic studies suggest that a conjugated allenone intermediate was generated in situ, which solves the problem of reactivity and regioselectivity of unsymmetrical dialkyl-substituted internal alkynes and enables the functionalisation of a broad range of substrates bearing electron-withdrawing functional groups. The resulting arylated 1,3-dicarbonyl compounds are versatile and useful building blocks for further functionalisation. This journal is
Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives
Sherwood, Alexander M.,Williamson, Samuel E.,Johnson, Stephanie N.,Yilmaz, Anil,Day, Victor W.,Prisinzano, Thomas E.
, p. 980 - 992 (2018/01/27)
A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated
Gold-catalyzed regioselective synthesis of 2- and 3-alkynyl furans
Li, Yifan,Brand, Jonathan P.,Waser, Jerome
supporting information, p. 6743 - 6747 (2013/07/26)
Chemical Matching: C2- or C3-alkynylated furans were selectively synthesized by using gold catalysis. Direct C-H alkynylation of furans was achieved with C2 selectivity, and a domino cyclization/alkynylation process starting from allenes gave C3-alkynylat
Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation
Shu, Chao,Liu, Meng-Qi,Sun, Yu-Zhe,Ye, Long-Wu
supporting information, p. 4958 - 4961,4 (2012/12/12)
A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.
