4709-59-5Relevant articles and documents
Chemoselective γ-Oxidation of β,γ-Unsaturated Amides with TEMPO
Heindl, Sebastian,Lemmerer, Miran,Malzer, Nicolas,Matyasovsky, Ján,Maulide, Nuno,Riomet, Margaux
supporting information, p. 19123 - 19127 (2021/07/26)
A chemoselective and robust protocol for the γ-oxidation of β,γ-unsaturated amides is reported. In this method, electrophilic amide activation, in a rare application to unsaturated amides, enables a regioselective reaction with TEMPO resulting in the title products. Radical cyclisation reactions and oxidation of the synthesised products highlight the synthetic utility of the products obtained.
Synthesis of Fasicularin
Kaga, Atsushi,Tnay, Ya Lin,Chiba, Shunsuke
supporting information, p. 3506 - 3508 (2016/07/26)
The synthesis of a tricyclic marine alkaloid, fasicularin, was accomplished. Stereoselective synthesis of the aza-spirocyclic BC-ring precursor and ensuing construction of the A-ring with stereocontrolled installation of the C2 hexyl group feature prominently in the synthesis.
Application of sulfuryl chloride for the quick construction of β-chlorotetrahydrofuran derivatives from homoallylic alcohols under mild conditions
Zeng, Xianghua,Miao, Chengxia,Wang, Shoufeng,Xia, Chungu,Sun, Wei
supporting information, p. 2391 - 2396 (2013/09/23)
An efficient and mild method is reported for the construction of β-chlorotetrahydrofuran derivatives by 5-endo chlorocycloetherification of homoallylic alcohols. The system employs sulfuryl chloride as the chlorinating agent under catalyst-free conditions. A variety of homoallylic alcohols with aryl or alkyl substituents were smoothly converted into β- chlorotetrahydrofurans in yields up to 98%.
BF3-promoted synthesis of spiroindenyl heterocycles
Chang, Meng-Yang,Lin, Chung-Han,Chen, Yeh-Long,Hsu, Ru-Ting,Chang, Ching-Yao
scheme or table, p. 3154 - 3158 (2010/08/07)
An easy and straightforward synthesis of spiroindenyl heterocycles by the repeated treatment of boron trifluoride etherate (BF3-OEt2) is reported. The overall transformation from ketones 1 to spiro-fused indenes 3 proceeds via Wittig olefination, deconjugation, Grignard addition, and intramolecular electrophilic cyclization in moderate yields. It presents a novel rearrangement reaction catalyzed by boron trifluoride etherate and broadens the scope of application.
Microwave-assisted regioselective olefinations of cyclic mono- and di-ketones with a stabilized phosphorus ylide
Wu, Jinlong,Li, Dan,Wu, Huafeng,Sun, Lijie,Dai, Wei-Min
, p. 4643 - 4650 (2007/10/03)
A number of cyclic mono- and di-ketones underwent regioselective olefination with (carbethoxyethylidene)triphenylphospharane under controlled microwave heating. The Wittig reaction of 4-substituted cyclohexanones or 1,2- and 1,4-cyclohexanediones with the ylide at 190 °C for 20 min in MeCN afforded the exocyclic olefins in >94:6 isomer ratios. On the other hand, the same reactions carried out at 230 °C for 20 min in the presence of 20 mol % DBU furnished the endocyclic olefins in >83:17 isomer ratios. The base-mediated isomerization of the exocyclic olefins into the endocyclic isomers was primarily driven by thermodynamic stability of the products and the effect of ring structures on deconjugation was examined.
New application of bromotrimethylsilane: Elaboration of aldehydes/ketones into homologous α,β-unsaturated esters via β-hydroxy esters
Suri, Suresh C.,Marcischak, Jacob C.
, p. 379 - 387 (2007/10/03)
α,β-Unsaturated esters are formed when β-hydroxy esters react with bromotrimethylsilane which is generated from chlorotrimethylsilane- lithium bromide in acetonitrile. Copyright Taylor & Francis, Inc.
Simplistic expedient and practical synthesis of (±)-α-lipoic acid
Chavan, Subhash P.,Shivsankar,Pasupathy
, p. 1297 - 1300 (2007/10/03)
Synthesis of α-lipoic acid has been achieved by a simple sequence of reactions. The synthesis highlights the use of α-chloroesters in a Reformatsky reaction. The intermediate keto acid is an intermediate from which both isomers of lipoic acid can be prepared. Georg Thieme Verlag Stuttgart.
Highly regioselective Wittig reactions of cyclic ketones with a stabilized phosphorus ylide under controlled microwave heating
Wu, Jinlong,Wu, Huafeng,Wei, Shaoyong,Dai, Wei-Min
, p. 4401 - 4404 (2007/10/03)
Significant base and temperature effects on the Wittig reactions of cyclohexanones with (carbethoxymethylene)triphenylphosphorane under microwave irradiation were observed. For the Wittig reactions carried out in a domestic microwave oven under solvent-free conditions, the initially formed exo-olefin products isomerized into the thermodynamically more stable endo-olefins due to uncontrolled high reaction temperature. In sharp contrast, under controlled microwave heating, both exo- and endo-olefins have been selectively synthesized by accurately regulating the reaction temperature with or without a base.
Heterogeneous Permanganate Oxidations: Synthesis of Medium Ring Keto-Lactones via Substituent Directed Oxidative Cyclisation
Das, Jagattaran,Chandrasekaran, Srinivasan
, p. 11709 - 11720 (2007/10/02)
Homoallyl alcohols 4a-b and 5a-b undergo smooth oxidative cyclisation to give the corresponding ring enlarged keto-lactones under heterogeneous permanganate oxidation conditions.
