433262-74-9Relevant academic research and scientific papers
Enantiodivergent Synthesis of Tertiary α-Aryl 1-Indanones: Evidence Toward Disparate Mechanisms in the Palladium-Catalyzed Decarboxylative Asymmetric Protonation
Kingston, Cian,Guiry, Patrick J.
, p. 3806 - 3819 (2017/04/13)
Herein, we describe a study into the scope and origin of an enantiodivergent effect in the palladium-catalyzed decarboxylative asymmetric protonation. By switching the achiral proton source, both enantiomers of a series of tertiary α-aryl-1-indanones are readily accessed from the corresponding α-aryl-β-keto allyl esters. In this example of dual stereocontrol, enantioselectivities up to 94% (S) and 92% (R) were achieved using Meldrum's acid and formic acid, respectively. In an attempt to rationalize this switch in absolute configuration an investigation of the ambiguous mechanism of the decarboxylative asymmetric protonation was conducted. A novel catalytic cycle for the reaction with formic acid is proposed and subjected to a variety of experimental studies.
Asymmetric microbial conversion of (E)-2-benzylideneindan-1-one by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata
Pinedo-Rivilla, Cristina,Aleu, Josefina,Collado, Isidro G.
experimental part, p. 1653 - 1657 (2012/01/30)
The transformation of (E)-2-benzylideneindan-1-one 1 by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata as biocatalysts was studied. The results showed the catalytic potential of these fungi in affording several hydroxylation a
Biocatalytic preparation and absolute configuration of enantiomerically pure fungistatic anti-2-benzylindane derivatives. Study of the detoxification mechanism by Botrytis cinerea
Pinedo-Rivilla, Cristina,Aleu, Josefina,Grande Benito, Manuel,Collado, Isidro G.
experimental part, p. 3784 - 3789 (2010/09/06)
Enantiomerically pure 2-benzylindane derivatives were prepared using biocatalytic methods and their absolute configuration determined. (1R,2S)-2-Benzylindan-1-ol ((1R,2S)-2) and (S)-2-benzylindan-1-one ((S)-3) were produced by fermenting baker's yeast. Li
Organocatalyzed enantioselective protonation of silyl enol ethers: Scope, limitations, and application to the preparation of enantioenriched homoisoflavones
Poisson, Thomas,Gembus, Vincent,Dalla, Vincent,Oudeyer, Sylvain,Levacher, Vincent
experimental part, p. 7704 - 7716 (2010/12/29)
In the present work, enantioselective protonation of silyl enol ethers is reported by means of a variety of chiral nitrogen bases as catalysts, mainly derived from cinchona alkaloids, in the presence of various protic nucleophiles as proton source. A detailed study of the most relevant reaction parameters is disclosed allowing high enantioselectivities of up to 92% ee with excellent yields to be achieved under mild and eco-friendly conditions. The synthetic utility of this organocatalytic protonation was demonstrated during the preparation of two homoisoflavones 4a and 4b, isolated from Chlorophytum Inornatum and Scilla Nervosa, which were obtained with 81% and 78% ee, respectively.
Organocatalytic enantioselective protonation of silyl enolates mediated by cinchona alkaloids and a latent source of HF
Poisson, Thomas,Dalla, Vincent,Marsais, Francis,Dupas, Georges,Oudeyer, Sylvain,Levacher, Vincent
, p. 7090 - 7093 (2008/09/17)
Hidden benefits: The enantioselective organocatalytic protonation of silyl enolates has been achieved by using readily available cinchona alkaloid catalysts (1) and a latent source of HF that delivers "at will" the active catalytic hydrogen fluoride salt
