15121-75-2Relevant academic research and scientific papers
A facile solid-phase synthesis of substituted 2(5H)-furanones with sulfone traceless linker
Sheng, Shou-Ri,Huang, Pei-Gang,Zhou, Wei,Luo, Hai-Rong,Lin, Shu-Ying,Liu, Xiao-Ling
, p. 2603 - 2605 (2004)
A novel solid-phase synthetic method for substituted 2(5H)-furanones with traceless sulfone linker strategy has been developed. The products were obtained in good yields and excellent purities.
CuCl-catalyzed cycloisomerization reaction of 1,2-allenyl carboxylic acids. A cost-effective synthesis of β-unsubstituted butenolides
Ma, Shengming,Yu, Zhanqian,Wu, Shulin
, p. 1585 - 1588 (2001)
Fourteen examples of 2,3-butadienoic acids were synthesized according to the known procedures and their high-yielding CuCl-catalyzed cycloisomerization reaction to afford butenolides were described.
Copper-Catalyzed Phosphorylation of 2,3-Allenoic Acids and Phosphine Oxide: Access to Phosphorylated Butenolides
Shen, Qitao,Yin, Chuanliu,Yu, Chuanming,Zheng, Xiangyun,Zhong, Tianshuo
, p. 9699 - 9710 (2021/07/26)
We investigated a novel Cu-catalyzed annulation of 2,3-allenoic acids with diphenylphosphine oxide, leading to the formation of 4-phosphate butenolides in up to 88% yield. The formation of the C-P bond provides new avenues for the functionalization of different furan-2(5H)-ones, with favorable features such as suitable functional group tolerance and mild synthesis conditions.
Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones
Shi, Zhanglin,Shen, Chaoren,Dong, Kaiwu
supporting information, p. 18039 - 18042 (2021/11/16)
Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.
Comparative studies of palladium and copper-catalysed γ-arylation of silyloxy furans with diaryliodonium salts
Alexander, Taylor S.,Clay, Travis J.,Maldonado, Bryan,Nguyen, Johny M.,Martin, David B.C.
, p. 2229 - 2238 (2019/03/06)
The γ-arylation of substituted silyl-activated butenolides has been studied using a broad scope of unsymmetrical hypervalent diaryliodonium salts via a palladium- or copper-catalysed coupling reaction, yielding interesting reactivity trends. The mild catalytic conditions and coupling partner variability provide access to synthetically useful building blocks toward the pursuit of aryl-lactone containing natural products and allows for facile diversification.
Lewis base-catalyzed electrophilic lactonization of selenyl bromide resin and facile solid-phase synthesis of furan-2(5H)-one derivatives
Jun He, Rong,Chun Zhu, Bing,Wang, Yu Guang
, p. 523 - 528 (2014/07/07)
A facile solid-phase synthesis approach was developed for the rapid synthesis of multi-substituted furan-2(5H)-one derivatives libraries. The synthetic strategy included the selenyl bromide resin-induced electrophilic lactonization catalyzed by Lewis base, lithiation, nucleophilic substitution and oxidation-elimination of the selenium resins. The advantages of the new method are good yields, high purity, straightforward operations and high diversity of the products, lack of odor, and good stability of the selenium resins. Copyright
Isothiourea-catalyzed asymmetric O- to C-carboxyl transfer of furanyl carbonates
Joannesse, Caroline,Morrill, Louis C.,Campbell, Craig D.,Slawin, Alexandra M. Z.,Smith, Andrew D.
, p. 1865 - 1879 (2011/08/05)
The ability of a chiral isothiourea to promote the regio- and enantioselective O- to C-carboxyl transfer of a series of 3-alkyl-5-aryl- and 5-methyl-3-phenylfuranyl carbonates is examined, generating preferentially the -regioisomers (α/γ up to 83:17) with high asymmetric induction (up to 83% ee). Georg Thieme Verlag Stuttgart - New York.
Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed γ-arylation strategy
Hyde, Alan M.,Buchwald, Stephen L.
supporting information; scheme or table, p. 2663 - 2666 (2009/10/02)
Methods for the construction of quaternary carbon centers are of great interest to synthetic chemists due to their presence in natural products. Development of the Pd-catalyzed arylation of butenolides with high selectivity for the γ-position allows for a
Pd(OAc)2-catalyzed cyclization of 2,3-allenoic acids in the presence of terminal αβ-unsaturated alkynones: A one-pot highly stereoselective synthesis of 4-(3′-oxo-1′(E)-alkenyl)-2(5H)- furanones
Chen, Guofei,Zeng, Rong,Gu, Zhenhua,Fu, Chunling,Ma, Shengming
supporting information; scheme or table, p. 4235 - 4238 (2009/06/06)
(Chemical Equation Presented) The Pd(OAc)2-catalyzed cyclization reaction of 2,3-allenoic acids in the presence of terminal αβ- unsaturated alkynones afforded an EIZ mixture of 4-(3′-oxo-1′- alkenyl)-2(5H)-furanones. A subsequent complete isomerization of the Z-isomer to E-isomer was observed in DMSO at 90 °C, which led to a highly stereoselective synthesis of 4-(3′-oxo-1′(E)-alkenyl)-2(5H)- furanones. A possible mechanism is proposed.
Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols and Amines: Selective Synthesis of Lactones and Lactams
Yoneda, Eiji,Zhang, Shi-Wei,Zhou, Da-Yang,Onitsuka, Kiyotaka,Takahashi, Shigetoshi
, p. 8571 - 8576 (2007/10/03)
Allenyl alcohols such as 4-hydroxybuta-1,2-dienes and 5-hydroxypenta-1,2-dienes having a variety of substituents undergo cyclocarbonylation in the presence of a ruthenium catalyst under mild conditions selectively to give five- and six-membered lactones in a high yield with 100% atom economy. 5-Aminopenta-1,2-dines are also cyclocarbonylated to give γ-lactams. A possible carbonylation mechanism involving a ruthenium cluster intermediate is proposed on the basis of experimental results.
