882161-47-9Relevant academic research and scientific papers
Auto Tandem Catalysis: Asymmetric Vinylogous Cycloaddition/Kinetic Resolution Sequence for the Enantioselective Synthesis of Spiro-Dihydropyranone from Benzylidene Meldrum's Acid
Bournaud, Chloée,Brière, Jean-Fran?ois,Guillot, Régis,Toffano, Martial,Vo-Thanh, Giang
, p. 4452 - 4458 (2021)
A catalytic enantioselective vinylogous domino reaction has been achieved from ketone-derived benzylidene Meldrum's acid and α-ketolactones to provide spirolactone dihydropyranones with more than 99% ee. An Auto Tandem Catalysis (ATC) process resulting fr
Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones
Wittmann, Stéphane,Martzel, Thomas,Pham Truong, Cong Thanh,Toffano, Martial,Oudeyer, Sylvain,Guillot, Régis,Bournaud, Chloée,Gandon, Vincent,Brière, Jean-Fran?ois,Vo-Thanh, Giang
supporting information, p. 11110 - 11114 (2021/04/09)
Upon Br?nsted base organocatalysis, ketone-derived alkylidene Meldrum's acids proved to be competent vinylogous platforms able to undergo a formal (4+2) cycloaddition reaction with dihydro-2,3-furandione, providing an unprecedented route to 3,6-dihydropyran-2-ones as spiro[4.5]decane derivatives with up to 98 % ee thanks to the commercially available Takemoto catalyst. Preliminary investigation showed that this reaction could be extended to other activated ketones, establishing these alkylidene Meldrum's acids as a novel C4-synthon in the vinylogous series.
Synthesis of Cyclopentadienes for Cyclopentadienyl Ligands via Cp*RhIII-Catalyzed Formal sp3C-H Activation/Spiroannulations
Wang, Yongzhuang,Huang, Xiaoli,Wang, Qin,Tang, Yuhai,Xu, Silong,Li, Yang
supporting information, p. 757 - 761 (2021/02/01)
An efficient Cp*RhIII-catalyzed formal C(sp3)-H activation/spiroannulation of alkylidene Meldrum's acids with alkynes has been developed using catalytical Cu(OAc)2 and air as the oxidant. This reaction demonstrates a new and straightforward approach to spirocyclopentadienes with Meldrum's acid moieties in good to excellent yields under mild reaction conditions with a broad substrate scope. Notably, this protocol provides a novel and straightforward approach to cyclopentadienes with various substitution patterns and the corresponding cyclopentadienyl-type ligands from simple substrates.
Expedient synthesis of complex γ-butyrolactones from 5-(1-arylalkylidene) meldrums acids via sequential conjugate alkynylation/Ag(I)-catalyzed lactonization
Ahmar, Siawash,Fillion, Eric
supporting information, p. 5748 - 5751 (2015/02/19)
The conjugate alkynylation of alkylidene Meldrums acids with alkynylalanes and alkynyl Grignards allows for the formation of propargylic all-carbon quaternary stereocenters in high yields. Ag2CO3-catalyzed intramolecular cyclization
Asymmetric synthesis of all-carbon benzylic quaternary stereocenters via conjugate addition to alkylidene and indenylidene Meldrum's acids
Wilsily, Ashraf,Fillion, Eric
supporting information; experimental part, p. 8583 - 8594 (2009/12/28)
(Chemical Equation Presented) A systematic study outlining the enantioselective 1,4-addition of dialkylzinc reagents to 5-(1-arylalkylidene) and indenylidene Meldrum's acids is presented. Variation of the aryl and alkyl groups present on the alkylidene wa
Application of Meldrum's acid in natural product synthesis. Synthesis of ar-turmerone and α-curcumene
Mahulikar,Mane
, p. 15 - 18 (2007/10/03)
Meldrum's acid (1) is employed in the synthesis of ar-turmerone (6) and α-curcumene (12). 1-(p-Tolyl)ethyl Meldrum's acid (3), synthesised by three different routes, was the key intermediate in these syntheses.
Asymmetric synthesis of all-carbon benzylic quaternary stereocenters via Cu-catalyzed conjugate addition of dialkylzinc reagents to 5-(1-arylalkylidene) Meldrum's acids
Fillion, Eric,Wilsily, Ashraf
, p. 2774 - 2775 (2007/10/03)
The asymmetric synthesis of all-carbon benzylic quaternary stereocenters has been successfully achieved through copper-catalyzed addition of dialkylzinc reagents to 5-(1-arylalkylidene) and 5-(dihydroindenylidene) Meldrum's acids in the presence of phosph
