Hydrogenation of 1,2-indanedione over heterogeneous cinchonidine-modified platinum catalysts

Abstract

Hydrogenation of the prochiral diketone, 1,2-indanedione was for the first time investigated using cinchonidine-modified Pt/ Al 2 O 3 as a catalyst. The influence of the reaction parameters on catalyst activity, regio-and enantioselectivity was studied revealing fully regioselective hydrogenation of the C(2)-keto group. Enantioselectivities of the (R)-versus (S)-2-hydroxy-1-indanone varied from low to moderate in favor of the (R)-enantiomer.A systematic study of enantioselective hydrogenation of 1,2-indanedione -a new substrate for chirally modified heterogeneous catalysts -over cinchonidine modified Pt/Al 2 O 3 is presented. The influence of the reaction parameters on activity, regio-and enantioselectivity was studied.

Synthesis of Chiral Catalyst Modifiers by Hydrosilylation of Cinchonidine and Their Application in the Hydrogenation of 1‐Phenylpropane‐1,2‐dione and Ethyl Pyruvate on a Supported Pt/Al2O3 Catalyst

“…Nevertheless, the results obtained here are promising, demonstrating unambiguously that the ee obtained with cinchonidine as the chiral modifier in the hydrogenation of A is by no means the maximum value obtainable and that by proper substituents in the distal position of the modifier, higher ee values can be achieved. In a separate study, [26] we have evaluated a series of 16 chiral catalyst modifiers derived from cinchonidine, cinchonine and quinine structures in the hydrogenation of A, none of which provided higher ee values in the first hydrogenation step as compared to the parent modifier (-)-cinchonidine.…”

One-pot synthesis of (R)-2-acetoxy-1-indanone from 1,2-indanedione combining metal catalyzed hydrogenation and chemoenzymatic dynamic kinetic resolution

“…A particular objective of our ongoing work is the development of selective, one-pot asymmetric synthesis protocols combining heterogeneous metal and enzyme based catalysts separable by filtration, ideally allowing robust access to chiral small molecules. [8][9][10] Vicinal hydroxy ketones serve as useful starting materials for various classes of industrially relevant compounds. [11][12][13][14][15][16] As shown recently, the vicinal hydroxy ketone, rac-2-hydroxy-1indanone IJrac-2), can be efficiently obtained by regioselective hydrogenation of the corresponding vicinal dione, 1,2-indanedione (1).…”

“…[11][12][13][14][15][16] As shown recently, the vicinal hydroxy ketone, rac-2-hydroxy-1indanone IJrac-2), can be efficiently obtained by regioselective hydrogenation of the corresponding vicinal dione, 1,2-indanedione (1). 9,10 In the absence of asymmetric induction, the hydrogenation reaction produces an equimolar mixture of the two 2-hydroxy-1-indanone enantiomers. In earlier work, we have investigated the chemoenzymatic dynamic kinetic resolution (DKR) of rac-2 by use of heterogeneous catalysts.…”

Estudos da diastereosseletividade da adição de nucleófilos ao grupo carbonila de β-cetossulfóxidos sulfanilados derivados da 1-indanona e 1-tetralona

“…2006, 1219.Tais aminoindanóis, assim como os 1-amino-2-tetralóis encontram aplicações também em catálise assimétrica, como auxiliares quirais e como agentes de resolução quiral28,29 . Sua síntese, em poucos passos, e com baixo custo, seria altamente desejável30 .A maioria dos protocolos de síntese conhecidos para os 1-amino-2-indanóis, de configuração definida, envolve o uso de catálise enzimática ou catálise homogênea, que muitas vezes são métodos caros em que os produtos são difíceis de separar da mistura reacional.Recuero, V.; Gonzalo, G.; Brieva, R.; Gotor, V. Eur. J. Org.…”