The DOI matches its Crossref record; 27 of the 27 references it cites were found in a registry or an index.
Chirality sensing using stereodynamic probes with distinct electronic circular dichroism output
Abstract
Circular dichroism (CD) spectroscopy is one of the most useful techniques for the stereochemical analysis of chiral biopolymers and fine chemicals. It has become invaluable for the assignment of the absolute configuration, the study of conformational isomers, and the determination of racemization kinetics of CD active chiral compounds. Molecular interactions between a nonracemic chiral substrate and a chromophoric, CD-silent probe that is achiral or exists as a racemic mixture of rapidly interconverting enantiomeric conformations or configurations can induce a strong, characteristic chiroptical readout. A covalent or noncovalent binding event that coincides with a well-defined asymmetric induction process can effectively imprint the chiral information of the substrate on the stereodynamic sensor and thus generate intense Cotton effects in the UV region of the latter. The probe can thus function as a stereochemical reporter unit and analysis of the CD spectrum often provides accurate information about the absolute configuration and enantiomeric composition of the substrate used. In this review, recent developments in circular dichroism analysis of chiral compounds with stereodynamic probes are described and particular emphasis is given to sensor design, chiral induction processes and applications scope.
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Cites
Chirality-Sensing Supramolecular Systems
Hembury, G. A., Borovkov, V. V., & Inoue, Y. (2008) · Chemical Reviews · doi:10.1021/cr050005k · Cited by 1,140
Rapid determination of enantiomeric excess: a focus on optical approaches
Leung, D., Kang, S. O., & Anslyn, E. V. (2011) · Chemical Society Reviews · doi:10.1039/c1cs15135e · Cited by 334
Induced circular dichroism by chiral molecular interaction
Allenmark, S. (2003) · Chirality · doi:10.1002/chir.10220 · Cited by 330
Porphyrins and metalloporphyrins: Versatile circular dichroic reporter groups for structural studies
Huang, X., Nakanishi, K., & Berova, N. (2000) · Chirality · doi:10.1002/(sici)1520-636x(2000)12:4<237::aid-chir10>3.0.co;2-6 · Cited by 268
Huang, X., Rickman, B. H., Borhan, B., Berova, N., & Nakanishi, K. (1998) · Journal of the American Chemical Society · doi:10.1021/ja973539e · Cited by 198
Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts
Berova, N., Pescitelli, G., Petrovic, A. G., & Proni, G. (2009) · Chemical Communications · doi:10.1039/b909582a · Cited by 198
Origin, Control, and Application of Supramolecular Chirogenesis in Bisporphyrin-Based Systems
Borovkov, V. V., Hembury, G. A., & Inoue, Y. (2004) · Accounts of Chemical Research · doi:10.1021/ar0302437 · Cited by 198
Borovkov, V. V., Lintuluoto, J. M., & Inoue, Y. (2001) · Journal of the American Chemical Society · doi:10.1021/ja0032982 · Cited by 176
A Simple Method for the Determination of Enantiomeric Excess and Identity of Chiral Carboxylic Acids
Joyce, L. A., Maynor, M. S., Dragna, J. M., da Cruz, G. M., Lynch, V. M., Canary, J. W., & Anslyn, E. V. (2011) · Journal of the American Chemical Society · doi:10.1021/ja205775g · Cited by 173
Furusho, Y., Kimura, T., Mizuno, Y., & Aida, T. (1997) · Journal of the American Chemical Society · doi:10.1021/ja970431q · Cited by 162
Absolute Configurational Assignments of Secondary Amines by CD-Sensitive Dimeric Zinc Porphyrin Host
Huang, X., Fujioka, N., Pescitelli, G., Koehn, F. E., Williamson, R. T., Nakanishi, K., & Berova, N. (2002) · Journal of the American Chemical Society · doi:10.1021/ja020520p · Cited by 162
Kurtán, T., Nesnas, N., Li, Y.-Q., Huang, X., Nakanishi, K., & Berova, N. (2001) · Journal of the American Chemical Society · doi:10.1021/ja010249w · Cited by 161
You, L., Pescitelli, G., Anslyn, E. V., & Bari, L. D. (2012) · Journal of the American Chemical Society · doi:10.1021/ja301252h · Cited by 146
Dragna, J. M., Pescitelli, G., Tran, L., Lynch, V. M., Anslyn, E. V., & Bari, L. D. (2012) · Journal of the American Chemical Society · doi:10.1021/ja211768v · Cited by 138
Li, X., Tanasova, M., Vasileiou, C., & Borhan, B. (2008) · Journal of the American Chemical Society · doi:10.1021/ja0752639 · Cited by 137
Kurtán, T., Nesnas, N., Koehn, F. E., Li, Y., Nakanishi, K., & Berova, N. D. (2001) · Journal of the American Chemical Society · doi:10.1021/ja010250v · Cited by 127
Proni, G., Pescitelli, G., Huang, X., Nakanishi, K., & Berova, N. D. (2003) · Journal of the American Chemical Society · doi:10.1021/ja036294g · Cited by 118
Superchi, S., Bisaccia, R., Casarini, D., Laurita, A., & Rosini, C. (2006) · Journal of the American Chemical Society · doi:10.1021/ja058552a · Cited by 114
One-pot multi-substrate screening in asymmetric catalysis
Gao, X., & Kagan, H. B. (1998) · Chirality · doi:10.1002/chir.19 · Cited by 77
Gawronski, J. K., Kaźmierczak, F., Gawrońska, K., Rychłewska, U., Nordén, B., & Holmén, A. (1998) · Journal of the American Chemical Society · doi:10.1021/ja982131u · Cited by 63
Katoono, R., Kawai, H., Fujiwara, K., & Suzuki, T. (2009) · Journal of the American Chemical Society · doi:10.1021/ja906810b · Cited by 62
A High-Throughput Screening Protocol for Fast Evaluation of Enantioselective Catalysts
Wolf, C., & Hawes, P. A. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo025534s · Cited by 51
Self-citationBarcena, H. S., Holmes, A. E., Zahn, S., & Canary, J. W. (2003) · Organic Letters · doi:10.1021/ol0275217 · Cited by 49
Novel α,α-disubstituted α-aminoacids with axial dissymmetry and their N- or C-protected derivatives
Mazaleyrat, J., Gaucher, A., SAVRDA, J., & Wakselman, M. (1997) · Tetrahedron Asymmetry · doi:10.1016/s0957-4166(97)00009-8 · Cited by 37
Enantioselective alkylation of aldehydes promoted by (S)-tyrosine-derived β-amino alcohols
Wolf, C., Francis, C. J., Hawes, P. A., & Shah, M. (2002) · Tetrahedron Asymmetry · doi:10.1016/s0957-4166(02)00469-x · Cited by 33
Self-citationFormaggio, F., Crisma, M., Toniolo, C., Tchertanov, L., Guilhem, J., Mazaleyrat, J., Gaucher, A., & Wakselman, M. (2000) · Tetrahedron · doi:10.1016/s0040-4020(00)00801-2 · Cited by 26
Tsukube, H., Hosokubo, M., Wada, M., Shinoda, S., & Tamiaki, H. (1999) · Journal of the Chemical Society Dalton Transactions · doi:10.1039/a806582i · Cited by 16
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Supramolecular Chirality in Self-Assembled Systems
Liu, M., Zhang, L., & Wang, T. (2015) · Chemical Reviews · doi:10.1021/cr500671p · Cited by 2,250
Kumarasamy, E., Raghunathan, R., Sibi, M. P., & Sivaguru, J. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00136 · Cited by 756
Tanaka, H., Inoue, Y., & Mori, T. (2018) · ChemPhotoChem · doi:10.1002/cptc.201800015 · Cited by 729
Chiral Metal–Organic Frameworks
Gong, W., Chen, Z., Dong, J., Liu, Y., & Cui, Y. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00740 · Cited by 579
Metadata
- Authors
- Wolf, C., & Bentley, K. W.
- Venue
- Chemical Society Reviews
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2013
- Volume
- 42
- Issue
- 12
- Pages
- 5408
- ISSN
- 0306-0012 (ISSN-L)
- 1460-4744
- OpenAlex
- W1984527206
- Cited by
- 349
- References
- 27
- FWCI
- 1.55
- Type
- journal article
- Language
- en
- Open access
- closed
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