35998-30-2Relevant academic research and scientific papers
Alternate Heme Ligation Steers Activity and Selectivity in Engineered Cytochrome P450-Catalyzed Carbene-Transfer Reactions
Chen, Kai,Zhang, Shuo-Qing,Brandenberg, Oliver F.,Hong, Xin,Arnold, Frances H.
, p. 16402 - 16407 (2018)
We report a biocatalytic platform of engineered cytochrome P450 enzymes to carry out carbene-transfer reactions using a lactone-based carbene precursor. By simply altering the heme-ligating residue, we obtained two enzymes that catalyze olefin cyclopropan
A two-phase bromination process using tetraalkylammonium hydroxide for the practical synthesis of α-bromolactones from lactones
Hosono, Kazumi,Kodama, Shintaro,Nomoto, Akihiro,Ochi, Takanori,Ogawa, Akiya,Tabuchi, Akihiro,Yamamoto, Yuki,Yamazaki, Kento
supporting information, p. 2906 - 2914 (2022/01/12)
A simple and efficient method for α-brominating lactones that affords α-bromolactones under mild conditions using tetraalkylammonium hydroxide (R4N) as a base was developed. Lactones are ring-opened with Br2 and a substoichiometric amount of PBr3, leading to good yields of the corresponding α-bromocarboxylic acids. Subsequent intramolecular cyclization over 1 h using a two-phase system (H2O/CHCl3) containing R4N afforded α-bromo lactones in good yields. This method can be applied at the 10 mmol scale using simple operations. α-Bromo-δ-valerolactone, which is extremely reactive and difficult to isolate, could be isolated and stored in a freezer for about one week using the developed method. Optimizing the solvent for environmentally friendly large-scale syntheses revealed that methyl ethyl ketone (MEK) was as effective. In addition, in situ-generated α-bromo-δ-valerolactone was directly converted into a sulfur-substituted functional lactone without difficulty by reacting it with a sulfur nucleophile in one pot without isolation. This new bromination system is expected to facilitate the industrial use of α-bromolactones as important intermediates.
Method for synthesizing 4-vinyl-2(5H)-furanone
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Paragraph 0023-0027, (2019/09/05)
The invention discloses a method for synthesizing 4-vinyl-2(5H)-furanone. The method comprises the following steps: step (1) taking and adding metal sodium into methanol, dripping thiophenol into themethanol, and then continuously adding alpha-bromo-gamma
Facile synthetic approaches to 1-thiocyclopropanecarboxylates
Zhang, Xiansheng,Wu, Jingwei,Liu, Yuqiang,Xie, Yafei,Liu, Changying,Wang, Jianwu,Zhao, Guilong
, p. 799 - 811 (2017/07/22)
Two facile synthetic approaches to the novel biologically interesting 1-thiocyclopropanecarboxylates starting from corresponding thiols were developed. Approach A involved five steps with the key steps being the SN2 reactions of thiols and α-br
Synthesis and in vitro antitumor activity of new butenolide-containing dithiocarbamates
Wang, Xiao-Juan,Xu, Hai-Wei,Guo, Lin-Lin,Zheng, Jia-Xin,Xu, Bo,Guo, Xiao,Zheng, Chen-Xin,Liu, Hong-Min
scheme or table, p. 3074 - 3077 (2011/06/26)
Three series of butenolide-containing dithiocarbamates were designed and synthesized. Their anti-tumor activity in vitro was evaluated. Among them compound I-14 exhibited broad spectrum anti-cancer activity against five human cancer cell lines with IC50 30 μM. Structure-activity relationship analysis showed that the introduction of dithiocarbamate side chains on the C-3 position of butenolide was crucial for anti-tumor activity.
Concise total synthesis of (-)-8-epigrosheimin
Yang, Haishen,Gao, Yuzhe,Qiao, Xiaoxiao,Xie, Longguan,Xu, Xiaohua
supporting information; experimental part, p. 3670 - 3673 (2011/09/15)
A highly efficient route was developed to synthesize (-)-8-epigrosheimin in four steps from aldehyde 2 based on a substrate-controlled method. The key steps of the synthesis included (1) a stereo- and regioselective allylation addition, (2) an intramolecular translactonization, and (3) an aldehyde-ene cyclization.
Enantioselective direct vinylogous michael addition of functionalized furanones to nitroalkenes catalyzed by an axially chiral guanidine base
Terada, Masahiro,Ando, Kenichi
supporting information; experimental part, p. 2026 - 2029 (2011/06/23)
The highly syn-diastereo- and enantioselective direct vinylogous Michael addition ofα-thio substituted furanones with conjugate nitroalkenes was demonstrated using an axially chiral guanidine base catalyst. The method provides facile access to enantioenriched α,γ-functionalized butenolides that can be further manipulated, thereby rendering them useful synthetic intermediates. 2011 American Chemical Society.
TiIV-catalyzed asymmetric sulfenylation of 1,3-dicarbonyl compounds
Jereb, Marjan,Togni, Antonio
, p. 9384 - 9392 (2008/09/21)
The electrophilic enantioselective sulfenylation of 1,3-dicarbonyl compounds with phenylsulfenyl chloride is effectively catalyzed by [Ti-(TADDOLato)] complexes. The corresponding products are obtained in moderate to high yields. The highest ee values (up to 97%) are obtained in toluene at room temperature and with a typical catalyst loading of 5mol%. Bulky ester groups and sterically undemanding substituents at the α-position were found to be crucial structural features of the starting materials in order to assure high enantioselectivity. The absolute configuration of one of the chiral products has been determined. The stereochemical course of the reaction is similar to that of analogous [Ti-(TADDOLato)]-catalyzed atom-transfer reactions. A common side-reaction the sulfenylated products undergo is a deacylation leading to racemic α-sulfenylated esters.
Preparation and palladium-catalysed cross-coupling reactions of 3-and 4-tributylstannylfuran-2(5H)-ones
Hollingworth, Gregory J.,Perkins, Gemma,Sweeney, Joseph
, p. 1913 - 1919 (2007/10/03)
Stannylfuranones 1 and 2 were prepared by ipso radical desulfurative stannylation of phenylsulfanylfuranones 3 and 16. Compounds 1 and 2 underwent Stille coupling reactions with aryl iodides to give 3- and 4-arylfuran-2(5H)-ones.
