The Thiazolium-Catalyzed Sila-Stetter Reaction: Conjugate Addition of Acylsilanes to Unsaturated Esters and Ketones
Тип публикации: Journal Article
Дата публикации: 2004-02-10
scimago Q1
wos Q1
white level БС1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
14982429
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Краткое описание
A new acyl anion addition reaction between acylsilanes and alpha,beta-unsaturated conjugate acceptors promoted by a nucleophilic organic catalyst has been disclosed. The 1,4-dicarbonyl products produced in this reaction are highly useful synthons. Neutral carbenes (or zwitterions) generated in situ from commercial thiazolium salts are used as effective catalysts for the reaction which is in contrast to established anionic catalysts typically employed to promote the required Brook rearrangement (1,2-silyl shift from carbon to oxygen) involved in the reported reaction. This process successfully utilizes acylsilanes as tunable acyl anion progenitors and is tolerant of a wide range of structural diversity on the acylsilane or the conjugate acceptor.
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Mattson A. E., Bharadwaj A. R., Scheidt K. A. The Thiazolium-Catalyzed Sila-Stetter Reaction: Conjugate Addition of Acylsilanes to Unsaturated Esters and Ketones // Journal of the American Chemical Society. 2004. Vol. 126. No. 8. pp. 2314-2315.
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Mattson A. E., Bharadwaj A. R., Scheidt K. A. The Thiazolium-Catalyzed Sila-Stetter Reaction: Conjugate Addition of Acylsilanes to Unsaturated Esters and Ketones // Journal of the American Chemical Society. 2004. Vol. 126. No. 8. pp. 2314-2315.
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TY - JOUR
DO - 10.1021/ja0318380
UR - https://doi.org/10.1021/ja0318380
TI - The Thiazolium-Catalyzed Sila-Stetter Reaction: Conjugate Addition of Acylsilanes to Unsaturated Esters and Ketones
T2 - Journal of the American Chemical Society
AU - Mattson, Anita E
AU - Bharadwaj, Ashwin R
AU - Scheidt, Karl A.
PY - 2004
DA - 2004/02/10
PB - American Chemical Society (ACS)
SP - 2314-2315
IS - 8
VL - 126
PMID - 14982429
SN - 0002-7863
SN - 1520-5126
ER -
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BibTex (до 50 авторов)
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@article{2004_Mattson,
author = {Anita E Mattson and Ashwin R Bharadwaj and Karl A. Scheidt},
title = {The Thiazolium-Catalyzed Sila-Stetter Reaction: Conjugate Addition of Acylsilanes to Unsaturated Esters and Ketones},
journal = {Journal of the American Chemical Society},
year = {2004},
volume = {126},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/ja0318380},
number = {8},
pages = {2314--2315},
doi = {10.1021/ja0318380}
}
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MLA
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Mattson, Anita E., et al. “The Thiazolium-Catalyzed Sila-Stetter Reaction: Conjugate Addition of Acylsilanes to Unsaturated Esters and Ketones.” Journal of the American Chemical Society, vol. 126, no. 8, Feb. 2004, pp. 2314-2315. https://doi.org/10.1021/ja0318380.
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