Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994
Publication type: Journal Article
Publication date: 2017-10-30
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
29027460
Organic Chemistry
Abstract
The stereoselective synthesis of mixed alkyl-aryl vicinal diamines was demonstrated by the use of 1,2-bis(2-hydroxyphenyl)-1,2-diaminoethene (hpen). A sequential addition of aryl and alkyl aldehyde to hpen gave a fused imidazolidine-dihydro-1,3-oxazine ring stereoselectively, which undergoes the diaza-Cope rearrangement to provide mixed vicinal diimines at elevated temperature in good yields and excellent stereoselectivity. We also showed that (+)-CP-99,994 can be readily prepared by the diaza-Cope rearrangement in overall 42% yield.
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Total citations:
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Citations from 2025:
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(14.29%)
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Kim M., Kim H., Chin J. Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994 // Journal of Organic Chemistry. 2017. Vol. 82. No. 23. pp. 12050-12058.
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Kim M., Kim H., Chin J. Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994 // Journal of Organic Chemistry. 2017. Vol. 82. No. 23. pp. 12050-12058.
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TY - JOUR
DO - 10.1021/acs.joc.7b01751
UR - https://doi.org/10.1021/acs.joc.7b01751
TI - Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994
T2 - Journal of Organic Chemistry
AU - Kim, Miji
AU - Kim, Hyung-Jun
AU - Chin, Jik
PY - 2017
DA - 2017/10/30
PB - American Chemical Society (ACS)
SP - 12050-12058
IS - 23
VL - 82
PMID - 29027460
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2017_Kim,
author = {Miji Kim and Hyung-Jun Kim and Jik Chin},
title = {Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.joc.7b01751},
number = {23},
pages = {12050--12058},
doi = {10.1021/acs.joc.7b01751}
}
Cite this
MLA
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Kim, Miji, et al. “Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994.” Journal of Organic Chemistry, vol. 82, no. 23, Oct. 2017, pp. 12050-12058. https://doi.org/10.1021/acs.joc.7b01751.