1132763-86-0Relevant academic research and scientific papers
The role of L-proline and co-catalysts in the enantioselectivity of oxa-Michael-Henry reactions
do Carmo, Lucas F.,Silva, Simone C.,Machado, Matheus V.,Prata, Paloma S.,Wisniewski, Alberto,Vidal, Diogo M.,Villar, José Augusto F.P.
, p. 893 - 903 (2019)
The use of L-proline derivatives employed in OXA-Michael-Henry tandem reactions has been an efficient method to produce enantiomerically enriched compounds. In this work it was carried out a study of the OXA-Michael-Henry reactions between salicylaldehyde
Enantioselective synthesis of 2-Aryl-3-nitro-2 H -chromenes catalyzed by a bifunctional thiourea
Zhang, Zhiguo,Jakab, Gergely,Schreiner, Peter R.
, p. 1262 - 1264 (2011)
A bifunctional thiourea-catalyzed tandem approach of oxa-Michael-aza-Henry- desulfonamidation was used to synthesize chiral 2-aryl-3-nitro-2H-chromenes. This method provides direct access to the corresponding products in moderate to good yields and enanti
Heterogeneous enantioselective synthesis of chromans: Via the oxa-Michael-Michael cascade reaction synergically catalyzed by grafted chiral bases and inherent hydroxyls on mesoporous silica surface
Wang, Shanshan,He, Jing,An, Zhe
, p. 8882 - 8885 (2017)
A heterogeneous enantioselective oxa-Michael-Michael reaction for the synthesis of chromans has been developed on a heterogeneous acid-base synergic catalyst with inherent silica as acidic sites and immobilized chiral amines as basic sites. Final products were afforded in selectivity of up to 98% and ee of 97% from 2-nitrovinyl phenol and 3-methyl-2-butenal. The heterogeneous synergistic catalytic mechanism has also been studied.
Augmentation of Enantioselectivity by Spatial Tuning of Aminocatalyst: Synthesis of 2-Alkyl/aryl-3-nitro-2 H-chromenes by Tandem Oxa-Michael-Henry Reaction
Bez, Ghanashyam,Mohanta, Rahul
, p. 4627 - 4636 (2020/05/01)
The asymmetric oxa-Michael addition of salicylaldehyde to conjugated nitroalkenes often suffers from poor reactivity and selectivity and a long reaction time. Because of the formation of an iminium ion with aminocatalyst, the nucleophilicity of the phenol
Asymmetric Direct Michael Reactions of Cyclohexanone with Aromatic Nitroolefins in Water Catalyzed by Novel Axially Unfixed Biaryl-Based Bifunctional Organocatalysts
Zhao, Hong-Wu,Yang, Zhao,Yue, Yuan-Yuan,Li, Hai-Long,Song, Xiu-Qing,Sheng, Zhi-Hui,Meng, Wei,Guo, Xiao-Yu
supporting information, p. 293 - 297 (2014/02/14)
A new family of axially unfixed biaryl-based water-compatible bifuctional organocatalysts were designed and synthesized for the asymmetric direct Michael reaction of cyclohexanone with various nitroolefins in water. One of the organocatalysts incorporates
One-pot enantioselective synthesis of 3-nitro-2H-chromenes catalyzed by a simple 4-hydroxyprolinamide with 4-nitrophenol as cocatalyst
Yin, Guohui,Zhang, Richeng,Li, Lei,Tian, Jun,Chen, Ligong
, p. 5431 - 5438 (2013/09/02)
The asymmetric domino oxa-Michael-Henry reaction of salicylaldehyde derivatives with trans-β-nitro olefins catalyzed by a readily available trans-4-hydroxy-L-prolinamide with 4-nitrophenol as an effective cocatalyst is presented. The corresponding 3-nitro
Synthesis of substituted chiral chromans via organocatalytic kinetic resolution of racemic 3-nitro-2-aryl-2H-chromenes with ketones catalyzed by pyrrolidinyl-camphor-derived organocatalysts
Magar, Dhananjay R.,Chen, Kwunmin
experimental part, p. 5810 - 5816 (2012/09/10)
Efficient kinetic resolution of racemic 2-aryl-3-nitro-2H-chromenes (1a-l) has been explored with the pyrrolidinyl-camphor derivative 2b as a bifunctional organocatalyst under neat conditions in the presence of AcOH at 0 °C. In general, the organocatalytic asymmetric Michael addition of ketones proceeded smoothly to give the functionalized Michael adducts (3a-n) with good-to-high diastereo- and enantioselectivities (up to 92:8 dr, 93% ee, and 47% yield). The less reactive chromenes (S)-1a-h, k, l and (R)-1i-j were recovered in high chemical yields and moderate optical purity (up to 42% chemical yield and 72% ee).
Efficient kinetic resolution of racemic 3-nitro-2H-chromene derivatives catalyzed by Takemoto's organocatalyst
Xie, Jian-Wu,Fan, Li-Ping,Su, Hong,Li, Xin-Sheng,Xu, Dong-Cheng
experimental part, p. 2117 - 2122 (2010/07/04)
Efficient kinetic resolution of racemic 3-nitro-2H-chromenes by bifunctional thiourea afforded optically active (R)-3-nitro-2H-chromene derivatives with moderate to good enantioselectivities, which simultaneously gave the multifunctional 3,4-diphenyl-3a-n
Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using l-pipecolinic acid and substituted guanidine organocatalysts
Das, Bhaskar C.,Mohapatra, Seetaram,Campbell, Philip D.,Nayak, Sabita,Mahalingam, Sakkarapalayam M.,Evans, Todd
supporting information; experimental part, p. 2567 - 2570 (2010/06/21)
Organocatalytic domino oxa-Michael/aldol reactions between salicylaldehyde with electron deficient olefins are presented. We screened guanidine, 1,1,3,3-tetramethylguanidine (TMG) and l-pipecolinic acid as organocatalysts for this transformation. 3-Substi
New pyrrolidine-triazole-based C2 symmetric organocatalysts and their utility in the asymmetric Michael reaction of β-nitrostyrenes and the synthesis of nitrochromenes
Karthikeyan, Thandavamurthy,Sankararaman, Sethuraman
experimental part, p. 2741 - 2745 (2009/04/07)
The synthesis of new C2 symmetric bis(pyrrolidine-triazole)-based organocatalysts and their utility in the asymmetric Michael reaction of β-nitrostyrenes with very high diastereo- and enantioselectivity in water without any additives is reporte
