The Vinylogous Intramolecular Morita−Baylis−Hillman Reaction: Synthesis of Functionalized Cyclopentenes and Cyclohexenes with Trialkylphosphines as Nucleophilic Catalysts
Тип публикации: Journal Article
Дата публикации: 2002-02-26
SCImago Q1
Tоп 10% SCImago
WOS Q1
БС1
SJR: 5.491
CiteScore: 22
Impact factor: 16.6
ISSN: 00027863, 15205126
PubMed ID:
11890766
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Краткое описание
The development of the vinylogous intramolecular Morita-Baylis-Hillman reaction for the synthesis of functionalized cyclopentenes and cyclohexenes is described. The reaction involves the trialkyphosphine-catalyzed cyclization of 1,6- or 1,7-diactivated 1,5-hexadienes or 1,6-heptadienes, containing carboxyaldehyde, methyl ketone, or methoxycarbonyl as the olefin activating groups. A representative example of this reaction is the Me(3)P-catalyzed cyclization of 1a in tert-amyl alcohol, which provides the substituted cyclopentene 2a in 95% yield and with 97:3 regioselectivity.
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Frank S. A., Mergott D. J., Roush W. R. The Vinylogous Intramolecular Morita−Baylis−Hillman Reaction: Synthesis of Functionalized Cyclopentenes and Cyclohexenes with Trialkylphosphines as Nucleophilic Catalysts // Journal of the American Chemical Society. 2002. Vol. 124. No. 11. pp. 2404-2405.
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Frank S. A., Mergott D. J., Roush W. R. The Vinylogous Intramolecular Morita−Baylis−Hillman Reaction: Synthesis of Functionalized Cyclopentenes and Cyclohexenes with Trialkylphosphines as Nucleophilic Catalysts // Journal of the American Chemical Society. 2002. Vol. 124. No. 11. pp. 2404-2405.
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TY - JOUR
DO - 10.1021/ja017123j
UR - https://doi.org/10.1021/ja017123j
TI - The Vinylogous Intramolecular Morita−Baylis−Hillman Reaction: Synthesis of Functionalized Cyclopentenes and Cyclohexenes with Trialkylphosphines as Nucleophilic Catalysts
T2 - Journal of the American Chemical Society
AU - Frank, Scott A
AU - Mergott, Dustin J.
AU - Roush, William R
PY - 2002
DA - 2002/02/26
PB - American Chemical Society (ACS)
SP - 2404-2405
IS - 11
VL - 124
PMID - 11890766
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2002_Frank,
author = {Scott A Frank and Dustin J. Mergott and William R Roush},
title = {The Vinylogous Intramolecular Morita−Baylis−Hillman Reaction: Synthesis of Functionalized Cyclopentenes and Cyclohexenes with Trialkylphosphines as Nucleophilic Catalysts},
journal = {Journal of the American Chemical Society},
year = {2002},
volume = {124},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/ja017123j},
number = {11},
pages = {2404--2405},
doi = {10.1021/ja017123j}
}
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MLA
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Frank, Scott A., et al. “The Vinylogous Intramolecular Morita−Baylis−Hillman Reaction: Synthesis of Functionalized Cyclopentenes and Cyclohexenes with Trialkylphosphines as Nucleophilic Catalysts.” Journal of the American Chemical Society, vol. 124, no. 11, Feb. 2002, pp. 2404-2405. https://doi.org/10.1021/ja017123j.
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