398142-14-8Relevant academic research and scientific papers
Synthesis of Novel C 2-Symmetric Sulfur-Based Catalysts: Asymmetric Formation of Halo- and Seleno-Functionalized Normal- and Medium-Sized Rings
Jana, Sadhan,Kumar, Sangit,Rathore, Vandana,Verma, Ajay
, p. 1667 - 1672 (2019/08/28)
The synthesis of novel, highly functionalized, C 2 -symmetric sulfur-based catalysts is developed and their catalytic applications are explored in asymmetric bromo-, iodo- and seleno-functionalizations of alkenoic acids. This protocol provides
Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents
Alazet, Sébastien,Le Vaillant, Franck,Nicolai, Stefano,Courant, Thibaut,Waser, Jerome
, p. 9501 - 9504 (2017/07/22)
A versatile synthesis of azidolactones through azidation and cyclization of carboxylic acids onto alkenes has been developed. Based on either photoredox or palladium catalysis, (1,1) and (1,2) azido lactones can be selectively synthesized. The choice of catalyst and benziodoxol(on)e reagent serving as azide source was essential to initiate either a radical or Lewis acid mediated process with divergent outcome. These transformations were carried out under mild conditions using a low catalyst loading and gave access to a large scope of azido lactones.
Cobalt-catalyzed oxidative cyclization of gem-disubstituted conjugated alkenols
Alves, Tania M.F.,Costa, Mateus O.,Bispo, Beatriz A.D.,Pedrosa, Fabiana L.,Ferreira, Marco A.B.
, p. 3334 - 3338 (2016/07/11)
Aryl gem-disubstituted conjugated alkenols underwent oxidative cyclization affording 2,5,5-trisubstituted tetrahydrofurans in reasonable yields and good diastereoselectivities using the reductive termination variation of the Mukaiyama aerobic oxidative reaction. Under oxidative termination, the same alkenols produced diols and ketonic by-products via the double hydration and beta-scission competing pathways. Furthermore, the differences in alkenol reactivity under the reductive and oxidative termination conditions were investigated.
Regioselective aerobic oxidative Heck reactions with electronically unbiased alkenes: Efficient access to α-alkyl vinylarenes
Zheng, Changwu,Stahl, Shannon S.
supporting information, p. 12771 - 12774 (2015/08/18)
Branched-selective oxidative Heck coupling reactions have been developed between arylboronic acids and electronically unbiased terminal alkenes. The reactions exhibit high catalyst-controlled regioselectivity favoring the less common branched isomer. The reactions employ a catalyst composed of Pd(TFA)2/dmphen (TFA = trifluoroacetate, dmphen = 2,9-dimethyl-1,10-phenanthroline) and proceed efficiently at 45-60 °C under 1 atm of O2 without requiring other additives. A broad array of functional groups, including aryl halide, allyl silane and carboxylic acids are tolerated.
Asymmetric bromolactonization using amino-thiocarbamate catalyst
Zhou, Ling,Tan, Chong Kiat,Jiang, Xiaojian,Chen, Feng,Yeung, Ying-Yeung
supporting information; experimental part, p. 15474 - 15476 (2011/02/21)
A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of γ-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.
Reagent-controlled stereoselective iodolactonizations
Haas, Juergen,Piguel, Sandrine,Wirth, Thomas
, p. 297 - 300 (2007/10/03)
Chemical equation presented Iodocyclizations are important transformations and among stereocontrolled iodocyclizations mostly substrate-controlled versions using a chiral auxiliary have been successfully investigated. This work reports on stereoselective
