Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes.
Publication type: Journal Article
Publication date: 2003-04-04
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
12658646
General Chemistry
Catalysis
Organic Chemistry
Abstract
Reactions of but-3-yn-2-one (2) with aldehydes 1 in the presence of a Lewis acid and dimethyl sulfide (3 a) predominantly gave (E)-alpha-(halomethylene)aldols 4-5 in high yields, while reactions of methyl propiolate (6 a) mainly afforded (Z)-3-halogeno-2-(hydroxymethyl)acrylates 7-8 in low to moderate yields. A reaction of dimethyl acetylenedicarboxylate (10) with 1 a in the presence of TiCl(4) and 1,1,3,3-tetramethylthiourea (3 c) produced maleate (E)-11 (40 %) and butenolide 12 (40 %). When a reaction of 6 a with 1 a was carried out in the presence of TiBr(4) and 3 a (0.2 equiv) at -20 degrees C for 60 h, 3-(methylthio)-2-(hydroxyalkyl)acrylate 9 a was obtained in an 8 % yield. Experiments were conducted in order to elucidate the formation mechanism of 9 a, and it was made clear that 9 a was formed via the processes of the Michael addition of sulfide 3 a to alkynoate 6 a and an aldol reaction with 1 a and demethylation.
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Total citations:
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Citations from 2024:
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GOST
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KINOSHITA S. et al. Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes. // Chemistry - A European Journal. 2003. Vol. 9. No. 7. pp. 1496-1502.
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KINOSHITA S., KINOSHITA H., Iwamura T., WATANABE S., KATAOKA T. Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes. // Chemistry - A European Journal. 2003. Vol. 9. No. 7. pp. 1496-1502.
Cite this
RIS
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TY - JOUR
DO - 10.1002/chem.200390169
UR - https://doi.org/10.1002/chem.200390169
TI - Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes.
T2 - Chemistry - A European Journal
AU - KINOSHITA, Sayaka
AU - KINOSHITA, Hironori
AU - Iwamura, Tatsunori
AU - WATANABE, SHIN-ICHI
AU - KATAOKA, Tadashi
PY - 2003
DA - 2003/04/04
PB - Wiley
SP - 1496-1502
IS - 7
VL - 9
PMID - 12658646
SN - 0947-6539
SN - 1521-3765
ER -
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BibTex (up to 50 authors)
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@article{2003_KINOSHITA,
author = {Sayaka KINOSHITA and Hironori KINOSHITA and Tatsunori Iwamura and SHIN-ICHI WATANABE and Tadashi KATAOKA},
title = {Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes.},
journal = {Chemistry - A European Journal},
year = {2003},
volume = {9},
publisher = {Wiley},
month = {apr},
url = {https://doi.org/10.1002/chem.200390169},
number = {7},
pages = {1496--1502},
doi = {10.1002/chem.200390169}
}
Cite this
MLA
Copy
KINOSHITA, Sayaka, et al. “Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes..” Chemistry - A European Journal, vol. 9, no. 7, Apr. 2003, pp. 1496-1502. https://doi.org/10.1002/chem.200390169.