Dynamic Kinetic Resolution of Azlactones by a Chiral N,N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups
Publication type: Journal Article
Publication date: 2018-07-26
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
30048141
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A dynamic kinetic resolution (DKR) of azlactones in the presence of benzoic acid and a binaphthyl-based N, N-4-dimethylaminopyridine (DMAP) derivative 1i having two amide groups at the 3,3'-positions of a binaphthyl unit is developed. The reaction proceeded smoothly with a wide range of azlactones to provide α-amino acid derivatives with good to high enantiomeric ratios (er's). A multigram-scale reaction (2.5 g) for the DKR of azlactone 2d was also demonstrated, and the resulting product was converted to unnatural α-amino acid 6d'.
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27
Total citations:
27
Citations from 2025:
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(11.11%)
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MANDAI H. et al. Dynamic Kinetic Resolution of Azlactones by a Chiral N,N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups // Organic Letters. 2018. Vol. 20. No. 16. pp. 4811-4814.
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MANDAI H., Hongo K., Fujiwara T., Fujii K., Mitsudo K., Suga S. Dynamic Kinetic Resolution of Azlactones by a Chiral N,N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups // Organic Letters. 2018. Vol. 20. No. 16. pp. 4811-4814.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.8b01960
UR - https://doi.org/10.1021/acs.orglett.8b01960
TI - Dynamic Kinetic Resolution of Azlactones by a Chiral N,N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups
T2 - Organic Letters
AU - MANDAI, Hiroki
AU - Hongo, Kohei
AU - Fujiwara, Takuma
AU - Fujii, Kazuki
AU - Mitsudo, Koichi
AU - Suga, Seiji
PY - 2018
DA - 2018/07/26
PB - American Chemical Society (ACS)
SP - 4811-4814
IS - 16
VL - 20
PMID - 30048141
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2018_MANDAI,
author = {Hiroki MANDAI and Kohei Hongo and Takuma Fujiwara and Kazuki Fujii and Koichi Mitsudo and Seiji Suga},
title = {Dynamic Kinetic Resolution of Azlactones by a Chiral N,N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.orglett.8b01960},
number = {16},
pages = {4811--4814},
doi = {10.1021/acs.orglett.8b01960}
}
Cite this
MLA
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MANDAI, Hiroki, et al. “Dynamic Kinetic Resolution of Azlactones by a Chiral N,N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups.” Organic Letters, vol. 20, no. 16, Jul. 2018, pp. 4811-4814. https://doi.org/10.1021/acs.orglett.8b01960.