A Simple and General Chiral Silicon Lewis Acid for Asymmetric Synthesis: Highly Enantioselective [3 + 2] Acylhydrazone−Enol Ether Cycloadditions
Тип публикации: Journal Article
Дата публикации: 2005-06-23
SCImago Q1
Tоп 10% SCImago
WOS Q1
БС1
SJR: 5.491
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
16011341
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Краткое описание
A highly diastereo- and enantioselective [3 + 2] acylhydrazone-enol ether cycloaddition mediated by a simple chiral silane Lewis acid is described. The reactions are highly practical, as demonstrated by a larger scale (5 g of the hydrazone) reaction in which the product was obtained after recrystallization in 93% yield and 99% ee. Evidence for a stepwise mechanism and a model for the asymmetric induction are presented, as well.
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Shirakawa S., Lombardi P. J., Leighton J. A Simple and General Chiral Silicon Lewis Acid for Asymmetric Synthesis: Highly Enantioselective [3 + 2] Acylhydrazone−Enol Ether Cycloadditions // Journal of the American Chemical Society. 2005. Vol. 127. No. 28. pp. 9974-9975.
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Shirakawa S., Lombardi P. J., Leighton J. A Simple and General Chiral Silicon Lewis Acid for Asymmetric Synthesis: Highly Enantioselective [3 + 2] Acylhydrazone−Enol Ether Cycloadditions // Journal of the American Chemical Society. 2005. Vol. 127. No. 28. pp. 9974-9975.
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TY - JOUR
DO - 10.1021/ja052307+
UR - https://doi.org/10.1021/ja052307
TI - A Simple and General Chiral Silicon Lewis Acid for Asymmetric Synthesis: Highly Enantioselective [3 + 2] Acylhydrazone−Enol Ether Cycloadditions
T2 - Journal of the American Chemical Society
AU - Shirakawa, Seiji
AU - Lombardi, Pamela J.
AU - Leighton, James
PY - 2005
DA - 2005/06/23
PB - American Chemical Society (ACS)
SP - 9974-9975
IS - 28
VL - 127
PMID - 16011341
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2005_Shirakawa,
author = {Seiji Shirakawa and Pamela J. Lombardi and James Leighton},
title = {A Simple and General Chiral Silicon Lewis Acid for Asymmetric Synthesis: Highly Enantioselective [3 + 2] Acylhydrazone−Enol Ether Cycloadditions},
journal = {Journal of the American Chemical Society},
year = {2005},
volume = {127},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/ja052307 },
number = {28},
pages = {9974--9975},
doi = {10.1021/ja052307+}
}
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MLA
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Shirakawa, Seiji, et al. “A Simple and General Chiral Silicon Lewis Acid for Asymmetric Synthesis: Highly Enantioselective [3 + 2] Acylhydrazone−Enol Ether Cycloadditions.” Journal of the American Chemical Society, vol. 127, no. 28, Jun. 2005, pp. 9974-9975. https://doi.org/10.1021/ja052307 .
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