Syntheses and crystal structures of the cinchona alkaloid derivatives used as ligands in the osmium-catalyzed asymmetric dihydroxylation of olefins
Тип публикации: Journal Article
Дата публикации: 1993-02-01
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Краткое описание
Experimental procedures for the preparation of two classes of derivatives of the cinchona alkaloids dihydroquinine and dihydroquinidine are described. Ligands (DHQ) 2 -PHAL, 1a, and (DHQD) 2 -PHAL, 2a, are conveniently synthesized in good yield by the reaction of the corresponding alkaloid with 1,4-dichlorophthalazine in the presence of K 2 CO 3 and KOH in refluxing toluene. Derivatives DHQ-PHN, 1b, and DHQD-PHN, 2b, are prepared through an Ullmann-type coupling between the 9-O-alkaloid sodium alkoxide and 9-iodophenanthrene in the presence of CuI and pyridine. Crystal structures for derivatives 2a and 2b are also presented. These four alkaloid derivatives serve as highly enantioselective ligands for the osmium tetraoxide catalyzed asymmetric dihydroxylation (AD) of olefins
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Amberg W. et al. Syntheses and crystal structures of the cinchona alkaloid derivatives used as ligands in the osmium-catalyzed asymmetric dihydroxylation of olefins // Journal of Organic Chemistry. 1993. Vol. 58. No. 4. pp. 844-849.
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Amberg W., Bennani Y. L., Chadha R. K., Crispino G. A., Davis W. D., Hartung J., Ogino Y., Shibata T., Sharpless K. B. Syntheses and crystal structures of the cinchona alkaloid derivatives used as ligands in the osmium-catalyzed asymmetric dihydroxylation of olefins // Journal of Organic Chemistry. 1993. Vol. 58. No. 4. pp. 844-849.
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TY - JOUR
DO - 10.1021/jo00056a015
UR - https://doi.org/10.1021/jo00056a015
TI - Syntheses and crystal structures of the cinchona alkaloid derivatives used as ligands in the osmium-catalyzed asymmetric dihydroxylation of olefins
T2 - Journal of Organic Chemistry
AU - Amberg, Willi
AU - Bennani, Youssef L.
AU - Chadha, Raj K
AU - Crispino, Gerard A.
AU - Davis, William D.
AU - Hartung, Jens
AU - Ogino, Yasukazu
AU - Shibata, Tomoyuki
AU - Sharpless, K. Barry
PY - 1993
DA - 1993/02/01
PB - American Chemical Society (ACS)
SP - 844-849
IS - 4
VL - 58
SN - 0022-3263
SN - 1520-6904
ER -
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@article{1993_Amberg,
author = {Willi Amberg and Youssef L. Bennani and Raj K Chadha and Gerard A. Crispino and William D. Davis and Jens Hartung and Yasukazu Ogino and Tomoyuki Shibata and K. Barry Sharpless},
title = {Syntheses and crystal structures of the cinchona alkaloid derivatives used as ligands in the osmium-catalyzed asymmetric dihydroxylation of olefins},
journal = {Journal of Organic Chemistry},
year = {1993},
volume = {58},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/jo00056a015},
number = {4},
pages = {844--849},
doi = {10.1021/jo00056a015}
}
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MLA
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Amberg, Willi, et al. “Syntheses and crystal structures of the cinchona alkaloid derivatives used as ligands in the osmium-catalyzed asymmetric dihydroxylation of olefins.” Journal of Organic Chemistry, vol. 58, no. 4, Feb. 1993, pp. 844-849. https://doi.org/10.1021/jo00056a015.