Remote chirality transfer in nucleophilic catalysis withN-(4-pyridinyl)-L-proline derivatives
Publication type: Journal Article
Publication date: 2002-12-04
scimago Q2
wos Q1
SJR: 0.682
CiteScore: 4.9
Impact factor: 3.0
ISSN: 08990042, 1520636X
PubMed ID:
12467046
Catalysis
Organic Chemistry
Drug Discovery
Spectroscopy
Pharmacology
Analytical Chemistry
Abstract
Chiral nucleophilic catalysts 5-15 were prepared starting from L-proline. Catalysts 9 and 14 promoted acylative kinetic resolution of racemic amino alcohol derivative 16 with selectivity factors of 8.1 and 11, respectively, at ambient temperature. Since chiral elements are not present in the catalytically active pyridine ring in these catalysts, chirality transfer from the remote stereogenic center to the reactive site (N-acylpyridinium) is suggested to be responsible for the differentiation between enantiomers.
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Total citations:
49
Citations from 2025:
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GOST
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Kawabata T. et al. Remote chirality transfer in nucleophilic catalysis withN-(4-pyridinyl)-L-proline derivatives // Chirality. 2002. Vol. 15. No. 1. pp. 71-76.
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Kawabata T., Stragies R., FUKAYA T., FUJI K. Remote chirality transfer in nucleophilic catalysis withN-(4-pyridinyl)-L-proline derivatives // Chirality. 2002. Vol. 15. No. 1. pp. 71-76.
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RIS
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TY - JOUR
DO - 10.1002/chir.10166
UR - https://doi.org/10.1002/chir.10166
TI - Remote chirality transfer in nucleophilic catalysis withN-(4-pyridinyl)-L-proline derivatives
T2 - Chirality
AU - Kawabata, T.
AU - Stragies, Roland
AU - FUKAYA, Takayuki
AU - FUJI, Kaoru
PY - 2002
DA - 2002/12/04
PB - Wiley
SP - 71-76
IS - 1
VL - 15
PMID - 12467046
SN - 0899-0042
SN - 1520-636X
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2002_Kawabata,
author = {T. Kawabata and Roland Stragies and Takayuki FUKAYA and Kaoru FUJI},
title = {Remote chirality transfer in nucleophilic catalysis withN-(4-pyridinyl)-L-proline derivatives},
journal = {Chirality},
year = {2002},
volume = {15},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002/chir.10166},
number = {1},
pages = {71--76},
doi = {10.1002/chir.10166}
}
Cite this
MLA
Copy
Kawabata, T., et al. “Remote chirality transfer in nucleophilic catalysis withN-(4-pyridinyl)-L-proline derivatives.” Chirality, vol. 15, no. 1, Dec. 2002, pp. 71-76. https://doi.org/10.1002/chir.10166.