Development of a Nazarov Cyclization/Wagner−Meerwein Rearrangement Sequence for the Stereoselective Synthesis of Spirocycles
Тип публикации: Journal Article
Дата публикации: 2007-06-08
scimago Q1
wos Q1
БС1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
17555319
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Краткое описание
A stereoselective Nazarov cyclization/Wagner−Meerwein rearrangement sequence for the synthesis of spirocyclic compounds was developed. While a range of different substrate types engaged in the cyclization/rearrangement sequence, it was found that different substrates underwent different reaction pathways. Depending on the substitution pattern of the substrate, the sequence was terminated by either a hydride shift or the shift of a vinyl or aryl group. It was also possible to install adjacent quaternary stereocenters using this protocol. The efficiency of the Wagner−Meerwein rearrangement was found to be dependent upon both the type and the amount of promoter used to generate the intermediate oxyallyl cation.
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Huang J., Frontier A. J. Development of a Nazarov Cyclization/Wagner−Meerwein Rearrangement Sequence for the Stereoselective Synthesis of Spirocycles // Journal of the American Chemical Society. 2007. Vol. 129. No. 26. pp. 8060-8061.
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Huang J., Frontier A. J. Development of a Nazarov Cyclization/Wagner−Meerwein Rearrangement Sequence for the Stereoselective Synthesis of Spirocycles // Journal of the American Chemical Society. 2007. Vol. 129. No. 26. pp. 8060-8061.
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TY - JOUR
DO - 10.1021/ja0716148
UR - https://doi.org/10.1021/ja0716148
TI - Development of a Nazarov Cyclization/Wagner−Meerwein Rearrangement Sequence for the Stereoselective Synthesis of Spirocycles
T2 - Journal of the American Chemical Society
AU - Huang, Jie
AU - Frontier, Alison J.
PY - 2007
DA - 2007/06/08
PB - American Chemical Society (ACS)
SP - 8060-8061
IS - 26
VL - 129
PMID - 17555319
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2007_Huang,
author = {Jie Huang and Alison J. Frontier},
title = {Development of a Nazarov Cyclization/Wagner−Meerwein Rearrangement Sequence for the Stereoselective Synthesis of Spirocycles},
journal = {Journal of the American Chemical Society},
year = {2007},
volume = {129},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/ja0716148},
number = {26},
pages = {8060--8061},
doi = {10.1021/ja0716148}
}
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MLA
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Huang, Jie, and Alison J. Frontier. “Development of a Nazarov Cyclization/Wagner−Meerwein Rearrangement Sequence for the Stereoselective Synthesis of Spirocycles.” Journal of the American Chemical Society, vol. 129, no. 26, Jun. 2007, pp. 8060-8061. https://doi.org/10.1021/ja0716148.