Diels-Alder reaction of α-substituted acrylates and α-(methylene)lactones: Conformation of dienophiles and endo/exo selectivity
Тип публикации: Journal Article
Дата публикации: 1994-01-01
scimago Q3
wos Q2
БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
Diels-Alder reaction of 1,6-bis(trimethylsilyloxy)-2,4-hexadiene with α-substituted acrylates and 5 to 7- and 9 to 11-membered α-(methylene)lactones has been carried out to examine correlation of dienophile structure with endo/exo selectivity. While the conformationally flexible acrylates produced cycloadducts of endo/exo = 59:41 to 74:26, the 5 to 7-membered lactones with rigid s-cis conjugate system provide cyloadducts of endo/exo = 13:87 to 32:68 and the 9 to 11-membered lactones which can take both s-cis and s-trans conformation afforded endo/exo ratios of 37:63 to 57:43.
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Takeda K., Imaoka I., YOSHII E. Diels-Alder reaction of α-substituted acrylates and α-(methylene)lactones: Conformation of dienophiles and endo/exo selectivity // Tetrahedron. 1994. Vol. 50. No. 37. pp. 10839-10848.
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Takeda K., Imaoka I., YOSHII E. Diels-Alder reaction of α-substituted acrylates and α-(methylene)lactones: Conformation of dienophiles and endo/exo selectivity // Tetrahedron. 1994. Vol. 50. No. 37. pp. 10839-10848.
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TY - JOUR
DO - 10.1016/S0040-4020(01)85696-9
UR - https://doi.org/10.1016/S0040-4020(01)85696-9
TI - Diels-Alder reaction of α-substituted acrylates and α-(methylene)lactones: Conformation of dienophiles and endo/exo selectivity
T2 - Tetrahedron
AU - Takeda, Kei
AU - Imaoka, Ikuhiro
AU - YOSHII, Eiichi
PY - 1994
DA - 1994/01/01
PB - Elsevier
SP - 10839-10848
IS - 37
VL - 50
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (до 50 авторов)
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@article{1994_Takeda,
author = {Kei Takeda and Ikuhiro Imaoka and Eiichi YOSHII},
title = {Diels-Alder reaction of α-substituted acrylates and α-(methylene)lactones: Conformation of dienophiles and endo/exo selectivity},
journal = {Tetrahedron},
year = {1994},
volume = {50},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/S0040-4020(01)85696-9},
number = {37},
pages = {10839--10848},
doi = {10.1016/S0040-4020(01)85696-9}
}
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MLA
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Takeda, Kei, et al. “Diels-Alder reaction of α-substituted acrylates and α-(methylene)lactones: Conformation of dienophiles and endo/exo selectivity.” Tetrahedron, vol. 50, no. 37, Jan. 1994, pp. 10839-10848. https://doi.org/10.1016/S0040-4020(01)85696-9.