An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines
Тип публикации: Journal Article
Дата публикации: 2003-03-28
SCImago Q1
Tоп 10% SCImago
WOS Q1
БС1
SJR: 5.491
CiteScore: 22
Impact factor: 16.6
ISSN: 00027863, 15205126
PubMed ID:
12696883
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Краткое описание
Ethyl 2-methyl-2,3-butadienoate acts as a 1,4-dipole synthon and undergoes [4 + 2] annulation with N-tosylimines in the presence of an organic phosphine catalyst. The resulting adducts, ethyl 6-substituted-1-(4-tosyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylates, are formed in excellent yields with complete regioselectivity. Mechanistic reasoning for this new annulation has led to an expansion of the reaction scope by employing ethyl 2-(substituted-methyl)-2,3-butadienoates to give ethyl 2,6-cis-disubstituted-1-(4-tosyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylates with high diastereoselectivities.
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ГОСТ
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Zhu X., Lan J., Kwon O. An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines // Journal of the American Chemical Society. 2003. Vol. 125. No. 16. pp. 4716-4717.
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Zhu X., Lan J., Kwon O. An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines // Journal of the American Chemical Society. 2003. Vol. 125. No. 16. pp. 4716-4717.
Цитировать
RIS
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TY - JOUR
DO - 10.1021/ja0344009
UR - https://doi.org/10.1021/ja0344009
TI - An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines
T2 - Journal of the American Chemical Society
AU - Zhu, Xue-Feng
AU - Lan, Jie
AU - Kwon, Ohyun
PY - 2003
DA - 2003/03/28
PB - American Chemical Society (ACS)
SP - 4716-4717
IS - 16
VL - 125
PMID - 12696883
SN - 0002-7863
SN - 1520-5126
ER -
Цитировать
BibTex (до 50 авторов)
Скопировать
@article{2003_Zhu,
author = {Xue-Feng Zhu and Jie Lan and Ohyun Kwon},
title = {An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines},
journal = {Journal of the American Chemical Society},
year = {2003},
volume = {125},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/ja0344009},
number = {16},
pages = {4716--4717},
doi = {10.1021/ja0344009}
}
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MLA
Скопировать
Zhu, Xue-Feng, et al. “An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines.” Journal of the American Chemical Society, vol. 125, no. 16, Mar. 2003, pp. 4716-4717. https://doi.org/10.1021/ja0344009.
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