194800-71-0Relevant academic research and scientific papers
Copper-Catalyzed Stereoselective Defluorinative Borylation and Silylation of gem-Difluoroalkenes
Tan, Dong-Hang,Lin,Ji, Wei-Wei,Zeng, Yao-Fu,Fan, Wen-Xin,Li, Qingjiang,Gao, Hui,Wang, Honggen
, p. 1032 - 1037 (2018/01/27)
The copper-catalyzed stereoselective defluorinative borylation and silylation of gem-difluoroalkenes was developed. The protocol led to the exclusive formation of Z type monofluoroalkenyl borons and silanes in generally good efficiency with broad substrat
One-Pot l-Proline-Mediated Stereoselective α-C(sp2)–H Fluorination of α,β-Unsaturated Aldehydes through Methoxyfluorination–Elimination
Zhou, Jiadi,Jiang, Xinpeng,Jin, Can,Guo, Zhicheng,Su, Bin,Su, Weike
, p. 3631 - 3634 (2017/07/22)
A one-pot, two-step l-proline-mediated stereoselective α-C(sp2)–H fluorination of α,β-unsaturated aldehydes towards their corresponding (Z)-α-fluoro-α,β-unsaturated aldehydes has been developed. The first step utilises Selectfluor as a fluorinating agent in CH3NO2/MeOH forming (Z)-α-fluoro-α,β-unsaturated aldehydes and their corresponding dimethyl acetals through methoxyfluorination-elimination. In the second step, water is added to promote the hydrolytic cleavage of the dimethyl acetals. The obtained (Z)-α-fluoro-α,β-unsaturated aldehydes were smoothly reduced to the corresponding alcohols by using NaBH4.
A new approach to the synthesis of (Z)-2-fluoro-2-alkenals via Wittig-type carbonyl condensation reactions of 2-(fluoromethyl)-4,4,6-trimethyl-1,3-oxazine phosphonium bromide
Kajjout, Mohammed,Smietana, Micha?l,Leroy, Jacques,Rolando, Christian
, p. 1658 - 1660 (2013/03/29)
We report here the transformation of aldehydes to their (Z)-α-fluoro-α,β-unsaturated aldehyde homologs by condensation with the phosphonium salt of the Meyer's oxazine obtained from bromofluoroacetonitrile. After methylation with trimethyloxonium tetrafluoroborate the quaternized oxazine is cleanly reduced to mostly Z 2-fluoro-2-alkenals by sodium borohydride at room temperature. This methodology is compatible with usual protecting groups and affords an efficient access to functionalized mostly Z 2-fluoro-2-alkenals derived from natural products and their corresponding (Z)-2-fluoro-2-alkenols.
Synthesis of fluorinated pseudopeptides: Metal mediated reversal of stereochemistry in diastereoselective addition of organometallic reagents to N-(tert-butanesulfinyl)-α-fluoroenimines
Pierry, Camille,Cahard, Dominique,Couve-Bonnaire, Samuel,Pannecoucke, Xavier
experimental part, p. 2378 - 2386 (2011/05/14)
The addition reaction of organometallic reagents to N-(tert-butanesulfinyl) -α-fluoroenimines was studied. Depending of the nature of the organometallic species (Grignard reagents or zincate complexes), we were able to control the configuration of the new
Diastereocontrolled addition of organometallic reagents to S-chiral N-(tert-butanesulfinyl)-α-fluoroenimines
Pierry, Camille,Zoute, Ludivine,Jubault, Philippe,Pfund, Emmanuel,Lequeux, Thierry,Cahard, Dominique,Couve-Bonnaire, Samuel,Pannecoucke, Xavier
scheme or table, p. 264 - 266 (2009/04/11)
Grignard and organolithium reagents efficiently react with (S)-N-(tert-butanesulfinyl)-α-fluoroenimines to provide chiral allylamines in excellent yields and with diastereomeric ratios of up to 96:4. Acidic removal of the sulfinyl group and simple functio
The first synthesis and reaction of β-ethoxy-α-fluoro-α- (phenylselanyl)ethene: Scandium or lanthanum triflate catalyzed α-fluoroformylalkenylation of aldehydes
Hatanaka, Fuminori,Tsuchiya, Miyuki,Yoshimatsu, Mitsuhiro
, p. 2191 - 2194 (2007/10/03)
We describe the first preparation of the hitherto unknown β-ethoxy-α-fluoro-α-(phenylselanyl)ethenes and the successful Lewis acid catalyzed α-fluoroformylalkenylation of non-enolizable aldehyde acetals to provide α,β-unsaturated aldehydes or acetals excl
Reaction of β-fluorovinamidinium salt with grignard reagents. Facile and efficient route to (Z)-α-fluoro-α,β-unsaturated aldehydes
Yamanaka, Hiroki,Odani, Yasumasa,Ishihara, Takashi,Gupton, John T.
, p. 6943 - 6946 (2007/10/03)
β-Fluorovinamidinium salt (1) reacted cleanly with a variety of Grignard reagents in tetrahydrofuran at room temperature, followed by acid workup, to produce the corresponding (Z)-α-fluoro-α,β-unsaturated aldehydes (3) in good to excellent yields.
