945537-04-2Relevant academic research and scientific papers
A highly regio- and stereoselective synthesis of ?±-fluorinated imides via fluorination of chiral enamides
Xu, Yan-Shuang,Tang, Yu,Feng, He-Jing,Liu, Ji-Tian,Hsung, Richard P.
supporting information, p. 572 - 575 (2015/03/04)
A highly ??-facial selective and regioselective fluorination of chiral enamides is described. The reaction involves an enantioselective fluorination exclusively at the electron-rich enamide olefin with N-F reagents such as Selectfluor and N-fluoro-benzenesulfonimide [NFSI] accompanied by trapping of the ?2-fluoro-iminium cationic intermediate with water. The resulting N,O-hemiacetal could be oxidized using Dess-Martin periodinane, leading to an asymmetric sequence for syntheses of chiral ?±-fluoro-imides and optically enriched ?±-fluoro-ketones.
A mutually π-facial selective cyclopropanation of chiral enamides using dirhodium(ll) carbenoids
Lu, Ting,Song, Zhenlei,Hsung, Richard P.
, p. 541 - 544 (2008/09/16)
A mutually π-facial selective cyclopropanation of chiral enamides using dirhodium(ll) carbenoids is described here. This work illustrates the influence of enamide substituents on stereoselectivity and reveals insights into this cyclopropanation.
Stereoselective Simmons-Smith cyclopropanation of chiral enamides
Song, Zhenlei,Lu, Ting,Hsung, Richard P.,Al-Rashid, Ziyad F.,Ko, Changhong,Tang, Yu
, p. 4069 - 4072 (2008/03/12)
(Chemical Equation Presented) Efficient and practical access to chiral aminocyclopropanes is secured by the title reaction (see example). Both E and Z enamides undergo the cyclopropanation with high diastereoselectivity (d.r. up to > 95:5). The applicatio
