- Cu(I)-Catalyzed Enantioselective Alkynylation of Thiochromones
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A highly efficient asymmetric synthesis of chiral thiochromanones is developed via Cu(I)/phosphoramidite catalyzed asymmetric alkynylation of thiochromones under mild reaction conditions. The catalyst system is tolerant of various thiochromone precursors and terminal alkynes. The established asymmetric transformation provides different enatiomeric-enriched thiochromanones with more molecular complexity and enables access to chiral thioflavanones, a subgroup of flavonoid by further functionalization.
- Chang, Xiaoyong,Lin, Zhenyang,Meng, Ling,Ngai, Ka Yan,Wang, Jun
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supporting information
p. 1155 - 1159
(2020/02/26)
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- Development of conjugate addition of lithium dialkylcuprates to thiochromones: Synthesis of 2-alkylthiochroman-4-ones and additional synthetic applications
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Lithium dialkylcuprates undergo conjugate addition to thiochromones to afford 2-alkylthiochroman-4-ones in good yields. This approach provide an efficient and general synthetic approach to privileged sulfur-containing structural motifs and valuable precursors for many pharmaceuticals, starting from common substrates-thiochromones. Good yields of 2-alkyl-substituted thiochroman-4-ones are attained with lithium dialkylcuprates, lithium alkylcyanocuprates or substoichiometric amount of copper salts. The use of commercially available inexpensive alkyllithium reagents will expedite the synthesis of a large library of 2-alkyl substituted thiochroman-4-ones for additional synthetic applications.
- Bass, Shekinah A.,Parker, Dynasty M.,Bellinger, Tania J.,Eaton, Aireal S.,Dibble, Angelica S.,Koroma, Kaata L.,Sekyi, Sylvia A.,Pollard, David A.,Guo, Fenghai
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supporting information
(2018/08/21)
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- Cu-Catalyzed Conjugate Addition of Grignard Reagents to Thiochromones: An Enantioselective Pathway for Accessing 2-Alkylthiochromanones
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The enantioselective incorporation of alkyl groups in thiochromones was realized for the first time by a Cu/(R, S)-PPF-P t Bu 2 -catalyzed conjugate addition of Grignard reagents to thiochromones. With this method, a series of 2-methylthiochromanones were obtained in good yields (up to 96% yield) with moderate-to-good ee values (up to 87% ee). The established method expedites the synthesis of a large library of chiral thiochromanones for further synthetic applications and biological studies.
- Luo, Shihui,Meng, Ling,Yang, Qingxiong,Wang, Jun
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supporting information
p. 2071 - 2075
(2018/09/18)
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- Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones
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A highly efficient asymmetric synthesis of chiral thioflavanones is developed via conjugate addition of arylzinc reagents to thiochromones using Rh(COD)Cl2/(R)-3,4,5-MeO-MeOBIPHEP catalyst. This method overcomes catalyst poisoning and substrate inertness and affords a series of chiral thioflavanones (2-arylthiochroman-4-ones) in good yields (up to 91% yield) with excellent ee values (up to 97% ee). The established asymmetric synthesis paves the way for further pharmaceutical studies.
- Meng, Ling,Jin, Ming Yu,Wang, Jun
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p. 4986 - 4989
(2016/10/14)
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- Synthesis and biochemical evaluation of thiochromanone thiosemicarbazone analogues as inhibitors of cathepsin L
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A series of 36 thiosemicarbazone analogues containing the thiochromanone molecular scaffold functionalized primarily at the C-6 position were prepared by chemical synthesis and evaluated as inhibitors of cathepsins L and B. The most promising inhibitors f
- Song, Jiangli,Jones, Lindsay M.,Kumar, G. D. Kishore,Conner, Elizabeth S.,Bayeh, Liela,Chavarria, Gustavo E.,Charlton-Sevcik, Amanda K.,Chen, Shen-En,Chaplin, David J.,Trawick, Mary Lynn,Pinney, Kevin G.
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experimental part
p. 450 - 453
(2012/09/25)
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- Fluoride ion-catalyzed conjugate addition for easy synthesis of 3-sulfanylpropionic acid from thiol and α,β-unsaturated carboxylic acid
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3-Sulfanylpropionic acids are obtained in excellent yields by proceeding through a simple, mild, and efficient procedure utilizing tetrabutylammonium fluoride (TBAF) as catalyst.
- Gao, Shijay,Tseng, Chi,Tsai, Cheng Hsuan,Yao, Ching-Fa
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p. 1955 - 1961
(2008/09/17)
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- Iodine catalyzed conjugate addition of mercaptans to α,β- unsaturated carboxylic acids under solvent-free condition
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We have described herein molecular iodine catalyzed Michael addition of thiol to α,β-unsaturated carboxylic acids. This environmentally benign catalytic system (iodine) used under mild and solvent-free conditions to achieve the corresponding adducts in excellent yield.
- Gao, Shijay,Tzeng, Tingkai,Sastry,Chu, Cheng-Ming,Liu, Ju-Tsung,Lin, Chunchi,Yao, Ching-Fa
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p. 1889 - 1893
(2007/10/03)
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- CONFORMATIONAL ANALYSIS AND PHOTOCHeMICAL BEHAVIOUR OF SULFOXIDES IN THE NAPHTHOTHIOPYRAN AND NAPHTHOTHIOPYRAN SERIES
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The sulfoxides derived from 2,3-dihydro-4H-naphthothiopyran and its 4-phenyl and 4-oxo derivatives, as well as the analogous sulfoxides in the 2,3-dihydro-1H-naphthothiopyran series, have been synthesized and their structures established by spectroscopic methods, especially 1H and 13C nmr.On the photolysis these sulfoxides have been found to react by a rather inefficient photochemical deoxygenation pathway.
- Still, Ian W. J.,Arora, Parkash C.,Hasan, S. Khaquan,Kutney, Gerald W.,Lo, LAwrence Y. T.,Turnbull, Kenneth
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p. 199 - 209
(2007/10/02)
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