Co-reporter:Gui Gao;Bing Zheng;Yue Fu;Minyan Li;Bo Wang;Xiang-Zhu Chen;Yuan-Yuan Zhang;Jing-Jing Liu;Shi-Cong Hou;Patrick J. Walsh
Asian Journal of Organic Chemistry 2017 Volume 6(Issue 6) pp:654-657
Publication Date(Web):2017/06/01
DOI:10.1002/ajoc.201700075
AbstractA palladium-catalyzed α-arylation reaction of unactivated sulfones with aryl chlorides is presented. High reactivity and chemoselectivity was achieved with a combination of Buchwald's 2nd generation palladium precatalyst and Kwong's indole-based phosphine ligand. A variety of aryl chlorides and aryl methyl sulfones were coupled in good to excellent yields. A gram-scale arylation was also successfully conducted. Chemoselective arylation of the sulfone was observed over Buchwald–Hartwig amination.
Co-reporter:Xiang-Zhu Chen;Xiao-Dong Ma;Hong-Mei Wang;Mian Wang;Yuan-Yuan Zhang;Gui Gao;Jing-Jing Liu;Shi-Cong Hou
New Journal of Chemistry (1998-Present) 2017 vol. 41(Issue 16) pp:8026-8030
Publication Date(Web):2017/08/07
DOI:10.1039/C7NJ00908A
A new coumarin-based fluorescent probe (P) has been developed for visual detection of Pd(II) ions, based on a striking color change from green to yellow and significant fluorescence quenching in the presence of Pd(II) ions. The probe shows high sensitivity and selectivity and a rapid response time to Pd(II) ions in aqueous medium, with a detection limit as low as 4.0 × 10−8 M. Fluorescence microscopy imaging of HeLa cells showed that this fluorescent probe is effective for detecting intracellular Pd(II) ions.
Co-reporter:Fei-Peng Liu, Jiang-Chun Zhong, Bing Zheng, Shuo-Ning Li, Gui Gao, Zhong-Yu Wang, Min-Yan Li, Shi-Cong Hou, Min Wang, Qing-Hua Bian
Tetrahedron: Asymmetry 2015 Volume 26(Issue 17) pp:961-965
Publication Date(Web):15 September 2015
DOI:10.1016/j.tetasy.2015.07.012
An efficient enantioselective total synthesis of an antitumor marine natural product (S,4E,15Z)-docosa-4,15-dien-1-yn-3-ol 1 with 96% ee and 15% overall yield has been achieved; this is the first preparation of 1 via asymmetric catalytic strategy. The key steps involve the asymmetric addition of trimethylsilylacetylene to a diolefinc aldehyde using a (R,R)-ProPhenol ligand and a zipper reaction of an alkyne.(S,4E,15Z)-Docosa-4,15-dien-1-yn-3-olC22H38OEe = 96%[α]D20 = +18.4 (c 0.10, MeOH)Source of chirality: (R,R)-ProPhenolAbsolute configuration: (S)
Co-reporter:Tingting Chai;Wenwen Yang;Jing Qiu
Chirality 2015 Volume 27( Issue 1) pp:32-38
Publication Date(Web):
DOI:10.1002/chir.22385
Abstract
The enantiomeric separation of eight pesticides including bitertanol (1), diclobutrazol (2), fenbuconazole (3), triticonazole (4), imazalil (5), triapenthenol (6), ancymidol (7), and carfentrazone-ethyl (8) was achieved, using normal-phase high-performance liquid chromatography on two cellulosed-based chiral columns. The effects of isopropanol composition from 2% to 30% in the mobile phase and column temperature from 5 to 40 °C were investigated. Satisfactory resolutions were obtained for bitertanol (1), triticonazole (4), imazalil (5) with the (+)-enantiomer eluted first and fenbuconazole (3) with the (—)-enantiomer eluted first on Lux Cellulose-2 and Lux Cellulose-3. (+)-Enantiomers of diclobutrazol (2) and triapenthenol (6) were first eluted on Lux Cellulose-2. (—)-Carfentrazone-ethyl (8) were eluted first on Lux Cellulose-2 and Lux Cellulose-3 with incomplete separation. Reversed elution orders were obtained for ancymidol (7). (+)-Ancymidol was first eluted on Lux Cellulose-2 while on Lux Cellulose-3 (—)-ancymidol was first eluted. The results of the elution order at different column temperatures suggested that column temperature did not affect the optical signals of the enantiomers. These results will be helpful to prepare and analyze individual enantiomers of chiral pesticides. Chirality 27:32–38, 2015. © 2014 Wiley Periodicals, Inc.
Co-reporter:Shuo-Ning Li, Ling-Lan Fang, Jiang-Chun Zhong, Jun-Jian Shen, Hao Xu, Yan-Qing Yang, Shi-Cong Hou, Qing-hua Bian
Tetrahedron: Asymmetry 2014 Volume 25(Issue 8) pp:591-595
Publication Date(Web):30 April 2014
DOI:10.1016/j.tetasy.2013.12.018
An efficient catalytic asymmetric synthesis of the CPB pheromone [(S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one] and its enantiomer was accomplished with 99% ee and in gram quantities from geraniol. The key steps in this procedure involve Sharpless asymmetric epoxidation and recrystallization of the 4-bromobenzoate from the CPB pheromone to improve its enantiomeric purity. Furthermore, the absolute configuration of the CPB pheromone enantiomer was confirmed as (R) for the first time by the X-ray crystallographic structure of its benzoate.(R)-1,3-Dihydroxy-3,7-dimethyl-6-octen-2-oneC10H18O3Ee = 99%[α]D20=-3.7 (c 1.0, CHCl3)Source of chirality: l-(+)-diethyl tartrateAbsolute configuration: (R)
