281676-87-7Relevant articles and documents
Proline and 1-(2-(benzoxazole-2-yl)phenyl)-3-phenylthiourea supramolecular organocatalyst in asymmetric aldol reactions
Díaz-Juárez, Verónica,Juaristi, Eusebio,López-Ruiz, Heraclio,Pérez-Estrada, Salvador,Pérez-Venegas, Mario,Reyes-Escobedo, Carlos Ernesto,Rojas-Lima, Susana
, (2021)
In this work we report the (S)-proline-thiourea 1 host–guest complex as an efficient catalyst in the enantioselective aldol rection of ketones with aldehydes. This host–guest complex performs well at 0 °C, in a non-polar solvent, such as toluene, or under
New and effective proline-based catalysts for asymmetric aldol reaction in water
Yorulmaz, Tugba,Aydogan, Feray,Yolacan, Cigdem
, p. 78 - 85 (2017)
New proline diamide organocatalysts with Pro-Phe peptide bonds were synthesized and their catalytic activities in asymmetric direct aldol reactions of aliphatic ketones with aromatic aldehydes were investigated. Catalyst 6a showed good enantioselectivity
Asymmetric aldol reactions catalyzed by the promiscuous aldo-ketoreductase enzyme
Bayat, Saadi,Abd Malek, Emilia,Yahaya, Normi M.,Salleh, Abu Bakar,Tejo, Bimo Ario,Abdul Rahman, Mohd Basyaruddin
, p. 6303 - 6306 (2014)
The promiscuous aldo-ketoreductase (AKR) enzyme is used as a sustainable biocatalyst for the first time to catalyze asymmetric aldol reactions in aqueous medium. The reactions between aromatic aldehydes and cyclic/acyclic ketones give the corresponding pr
Homochiral bifunctional L-prolinamide- and L-bis-prolinamide-catalyzed asymmetric aldol reactions performed in wet solvent-free conditions
Anaya de Parrodi, Cecilia,Domínguez-Huerta, Alejandra,Hernández Pérez, Julio M.,Huelgas, Gabriela,Rojas Cabrera, Haydee,Sabala, Rocío,Somanathan, Ratnasamy,de la Higuera Macías, Maximiliano
supporting information, p. 22 - 36 (2020/12/04)
In this study, the novel bifunctional homochiral thiourea-L-prolinamides 1–4, tertiary amino-L-prolinamide 5, and bis-L-prolinamides 6 and 7 were prepared from enantiomerically pure (11R,12R)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene 8 and (11S,12S
Pro-phe derivatives as organocatalysts in asymmetric aldol reaction
Aydogan, Feray,Karaoglu, Merve,Yolacan, Cigdem
supporting information, p. 233 - 239 (2021/03/19)
The aldol reaction which is the most important one among the C-C bond forming reactions, is widely used by synthetic organic chemists to obtain β-hydroxycarbonyl compounds which are important starting components for biologically active compounds in optica
Proline-Histidine Dipeptide: A Suitable Template for Generating Ion-Tagged Organocatalysts for the Asymmetric Aldol Reaction
Inani, Heena,Singh, Avtar,Bhati, Meeta,Kumari, Kiran,Kucherenko, Alexander S.,Zlotin, Sergei G.,Easwar, Srinivasan
, p. 2702 - 2712 (2021/06/02)
Proline-histidine dipeptide laid the foundation for the construction of three new ion-tagged organocatalysts, utilising the imidazole moiety of histidine for generating the quaternary species. A brief comparative investigation of the catalysts in the enam
New small γ-turn type: N -primary amino terminal tripeptide organocatalyst for solvent-free asymmetric aldol reaction of various ketones with aldehydes
Begum, Zubeda,Kwon, Eunsang,Nakano, Hiroto,Okuyama, Yuko,Seki, Chigusa,Takeshita, Mitsuhiro,Thiyagarajan, Rajkumar,Tokiwa, Michio,Tokiwa, Suguru,Uwai, Koji
, p. 38925 - 38932 (2021/12/20)
New small γ-turn type N-primary amino terminal tripeptides were synthesized and their functionality as an organocatalyst was examined in the asymmetric aldol reaction of various ketones with different aromatic aldehydes under solvent-free neat conditions to afford the desired chiral anti-aldol products in good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn?:?anti/13?:?87 dr, up to 99% ee). This journal is
A chemo-enzymatic oxidation/aldol sequential process directly converts arylbenzyl alcohols and cyclohexanol into chiral β-hydroxy carbonyls
Cheng, Qipeng,Li, Hongyu,Liu, Guohua,Su, Yu,Tan, Chunxia,Wang, Chengyi,Wang, Yu,Xiao, Rui
supporting information, p. 7773 - 7779 (2021/10/12)
The development of a combination enzyme and organocatalyst for aqueous sequential organic transformation has great significance, in that it is not only environmentally friendly but also overcomes only a single methodological drawback, either in the chemical or biological process. Herein, through the utilization of the bulky steric hindrance of chiral proline derivatives, an integrated laccase and proline as a chemo-enzymatic co-catalyst system is developed. It enables an efficient oxidation/aldol enantioselective sequential reaction to be accomplished, overcoming the mutual deactivation issue. As we present in this study, this one-pot organic transformation, an initial laccase-mediated oxidation of arylbenzyl alcohols and cyclohexanol to form aldehydes and cyclohexanone, followed by a subsequent proline derivative-catalyzed aldol condensation of the in situ generated intermediates, provides various 1,2-diastereoisomeric chiral β-hydroxy ketones with acceptable yields and high enantio-/diastereoselectivities.
Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System
Rani, Dhiraj,Sethi, Aaftaab,Kaur, Khushwinder,Agarwal, Jyoti
, p. 9548 - 9557 (2020/09/09)
For the first time, an inclusion complex has been crafted between a carbohydrate-based molecule and a β-cyclodextrin (CD) hydrophobic cavity for asymmetric catalytic applications. This novel d-glucosamine-based inclusion compound has been synthesized in h
New Mesoporous silica-supported organocatalysts based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, reusable, and heterogeneous catalysts for the asymmetric aldol reaction
Juaristi, Eusebio,Romero-Sedglach, Kevin A.,Sánchez-Antonio, Omar,Vázquez-Orta, Erika C.
, (2020/10/18)
Novel organocatalytic systems based on the recently developed (S)-proline derivative (2S)-[5-(benzylthio)-4-phenyl-(1,2,4-triazol)-3-yl]-pyrrolidine supported on mesoporous silica were prepared and their efficiency was assessed in the asymmetric aldol rea
