Direct Monitoring of the Asymmetric Induction of Solid-Phase Catalysis Using Circular Dichroism: Diamine–CuI-Catalyzed Asymmetric Henry Reaction

2006 ◽  
Vol 45 (36) ◽  
pp. 5978-5981 ◽  
Author(s):  
Takayoshi Arai ◽  
Masahiko Watanabe ◽  
Akitsugu Fujiwara ◽  
Naota Yokoyama ◽  
Akira Yanagisawa
Keyword(s):  
Circular Dichroism ◽  
Solid Phase ◽  
Asymmetric Induction ◽  
Henry Reaction ◽  
Circular Dichroïsm

Direct Monitoring of the Asymmetric Induction of Solid-Phase Catalysis Using Circular Dichroism: Diamine–CuI-Catalyzed Asymmetric Henry Reaction

2006 ◽  
Vol 118 (36) ◽  
pp. 6124-6127 ◽  
Author(s):  
Takayoshi Arai ◽  
Masahiko Watanabe ◽  
Akitsugu Fujiwara ◽  
Naota Yokoyama ◽  
Akira Yanagisawa
Keyword(s):  
Circular Dichroism ◽  
Solid Phase ◽  
Asymmetric Induction ◽  
Henry Reaction ◽  
Circular Dichroïsm

Optical Activity of Symmetric Compounds in Chiral Media. I. Induced Circular Dichroism of Unbound Substrates

1971 ◽  
Vol 49 (4) ◽  
pp. 624-631 ◽  
Author(s):  
L. D. Hayward ◽  
R. N. Totty
Keyword(s):  
Circular Dichroism ◽  
Carbonyl Compounds ◽  
Optical Rotation ◽  
Optically Active ◽  
Asymmetric Induction ◽  
Azo Compounds ◽  
Induced Circular Dichroism ◽  
Chiral Media ◽  
Circular Dichroïsm ◽  
Rotational Strengths

In the presence of chiral environment compounds, C, optical rotation is induced in symmetric substrates, S, and may be detected as circular dichroism in the electronic spectra of the solutions. Thus the n − π* transitions of symmetric and racemic carbonyl compounds, and of symmetric nitro and azo compounds, become optically active when these S are dissolved in chiral hydrocarbons, ketones, or carbinols, or in solutions of these C in achiral solvents. The rotational strengths of the induced circular dichroism bands of S are solvent, temperature, and concentration dependent. Only limited correlation of the sign and magnitude of the induced bands with the stereochemistry of C and S is evident on the data so far accumulated. Halogenated achiral solvents enhance the intensity, and, in some cases reverse the sign of the induced bands.A new mechanism of asymmetric induction is proposed in which specific bonding of C with S is not prerequisite.

scholarly journals Solid-Phase Synthesis and Circular Dichroism Study of β-ABpeptoids

Molecules ◽  
2019 ◽  
Vol 24 (1) ◽  
pp. 178 ◽  
Author(s):  
Ganesh A. Sable ◽  
Kang Ju Lee ◽  
Hyun-Suk Lim
Keyword(s):  
Circular Dichroism ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Nmr Studies ◽  
Phase Synthesis ◽  
Methyl Group ◽  
Wide Range ◽  
Material Sciences ◽  
Folded Structures ◽  
Circular Dichroïsm

The development of peptidomimetic foldamers that can form well-defined folded structures is highly desirable yet challenging. We previously reported on α-ABpeptoids, oligomers of N-alkylated β2-homoalanines and found that due to the presence of chiral methyl groups at α-positions, α-ABpeptoids were shown to adopt folding conformations. Here, we report β-ABpeptoids having chiral methyl group at β-positions rather than α-positions as a different class of peptoids with backbone chirality. We developed a facile solid-phase synthetic route that enables the synthesis of β-ABpeptoid oligomers ranging from 2-mer to 8-mer in excellent yields. These oligomers were shown to adopt ordered folding conformations based on circular dichroism (CD) and NMR studies. Overall, these results suggest that β-ABpeptoids represent a novel class of peptidomimetic foldamers that will find a wide range of applications in biomedical and material sciences.

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