874948-60-4Relevant academic research and scientific papers
Hypercrosslinking chiral Br?nsted acids into porous organic polymers for efficient heterogeneous asymmetric organosynthesis
Jia, Ji,Liu, Xiaoming,Ma, Si,Xia, Hong,Zhang, Yuwei,Zhang, Zhenwei
supporting information, p. 25369 - 25373 (2021/12/07)
Here, we developed a construction strategy for directly immobilizing the axially chiral phosphoric acid into hypercrosslinked polymers by a one-pot Friedel-Crafts alkylation reaction. The obtained chiral polymers have high porosity, excellent stability and tailorable catalytic centers, and display excellent activity, enantioselectivity and recyclability for asymmetric transfer hydrogenation.
Synthesis of novel chiral phosphoric acid-bearing two acidic phenolic hydroxyl groups and its catalytic evaluation for enantioselective Friedel-Crafts alkylation of indoles and enones
Liu, Xiong-Li,Yu, Zhang-Biao,Pan, Bo-Wen,Chen, Lin,Feng, Ting-Ting,Zhou, Ying
, p. 628 - 634 (2015/03/30)
A novel chiral phosphoric acid catalyst bearing two acidic phenolic hydroxyl groups was synthesized. Its catalytic activity as a chiral Br?sted acid has been examined in the enantioselective Friedel-Crafts alkylation of indoles and enones as a model reaction. In comparison with the other chiral phosphoric acid catalysts, the reaction catalyzed by the novel chiral catalyst afforded the desired 3-substituted indoles in a higher enantioselectivity (up to 69% ee).
Biomimetic asymmetric 1,3-dioplar cycloaddition: Amino acid precursors in biosynthesis serve as latent azomethine ylides
Guo, Chang,Song, Jin,Gong, Liu-Zhu
supporting information, p. 2676 - 2679 (2013/07/19)
The first asymmetric catalytic biomimetic three-component 1,3-dipolar cycloaddition of α-keto esters and benzylamine with electron-deficient olefins, inspired by the transamination of α-keto acids involving pyridoxal phosphate (PLP)-dependent enzymes in biological systems, giving several families of structurally diverse pyrrolidine derivatives in high yields and excellent enantioselectivities (up to 99% ee) under mild conditions is described.
Chiral phosphoric acid catalyzed asymmetric friedel-crafts alkylation of indoles with nitroolefins
Tang, Hong-Ying,Zhang, Zhong-Biao
experimental part, p. 2038 - 2046 (2011/11/30)
Asymmetric Michael-type Friedel-Crafts (F-C) alkylations of indoles with nitroolefins catalyzed by a chiral H8-BINOL-based phosphoric acid were investigated. The reactions took place very smoothly in the presence of only 5 mol-% of catalyst at
Facile and efficient enantioselective strecker reaction of ketimines by chiral sodium phosphate
Shen, Ke,Liu, Xiaohua,Cai, Yunfei,Lin, Lili,Feng, Xiaoming
supporting information; scheme or table, p. 6008 - 6014 (2010/02/28)
A facile and efficient enantioselective Strecker reaction of ketimines catalyzed by a chiral alkali-metal salt has been developed. When 10 mol% BNPNa (BNP=1,1'-binaphthyl-2,2'-diylphosphate) prepared in situ and 10 mol% para-tert-butylortho-adamantylphenol (PBAP) were introduced into the reaction, up to 96% yield and up to 95% ee (ee=enantiomeric excess) were obtained. Both aliphatic and aromatic ketimines, especially sterically bulky cyclic ketimines derived from β-acetonaphthone, α-indanone, and α-tetralone were found suitable for this reaction. On the basis of the experimental results and previous reports, trimethylsilyl cyanide (TMSCN) was indicated to be the real reactive nucleophile despite the existence of PBAP, and a possible working model was proposed to explain the origin of the asymmetric induction. The facile availability of 1,1'-binaphthyl-2,2'-diylphosphoric acid (BNPH) and the simplicity of the procedure are beneficial for practical applications.
Organocatalytic synthesis of spiro[pyrrolidin-3,3′-oxindoles] with high enantiopurity and structural diversity
Chen, Xiao-Hua,Wei, Qiang,Luo, Shi-Wei,Xiao, Han,Gong, Liu-Zhu
supporting information; experimental part, p. 13819 - 13825 (2009/12/29)
The privileged spiro[pyrrolidin-3,3′-oxindole] derivatives exhibit important biological activities. An enantioselective organocatalytic approach to the rapid synthesis of spiro[pyrrolidin-3,3′-oxindole] derivatives with high enantiopurity and structural d
Chiral phosphoric acid catalyzed asymmetric Friedel-Crafts alkylation of indoles with simple α,β-unsaturated aromatic ketones
Tang, Hong-Ying,Lu, Ai-Dang,Zhou, Zheng-Hong,Zhao, Guo-Feng,He, Lian-Nian,Tang, Chu-Chi
experimental part, p. 1406 - 1410 (2009/04/04)
Asymmetric Michael-type Friedel-Crafts (F-C) alkylations of indoles with nonchelating α,β-unsaturated aromatic ketones catalyzed by a chiral H8-BINOL-based phosphoric acid were investigated. The reactions took place smoothly in the presence of
ASYMMETRIC-SYNTHESIS CATALYST BASED ON CHIRAL BROENSTED ACID AND METHOD OF ASYMMETRIC SYNTHESIS WITH THE CATALYST
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Page/Page column 19, (2010/11/08)
A compound usable as an asymmetric synthesis catalyst which can be easily synthesized without using any metal such as a lanthanoid group element; a method of asymmetric synthesis with the compound; and a chiral compound obtained by the asymmetric synthesis method. A Broensted acid is used as a catalyst in asymmetric synthesis, the chiral Broensted acid being represented by formula (1) below or formula (3) below. The asymmetric synthesis method employs the catalyst. Asymmetric synthesis with the catalyst gives a chiral compound.
Enantioselective organocatalytic reductive amination
Storer, R. Ian,Carrera, Diane E.,Ni, Yike,MacMillan, David W. C.
, p. 84 - 86 (2007/10/03)
The first enantioselective organocatalytic reductive amination reaction has been accomplished. The development of a new chiral phosphoric acid catalyst has provided a convenient strategy for the enantioselective construction of protected primary amines an
