Double Addition of Grignard Reagents to N-Glycosyl Nitrones: A New Tool for the Construction of Enantiopure Azaheterocycles
Publication type: Journal Article
Publication date: 2004-12-29
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
15646987
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
[Reaction: see text] C-Phenyl-N-erythrosylnitrone 3 behaves as a C1,C1' bis-electrophile, undergoing a double addition of Grignard reagents in a domino fashion to afford acyclic hydroxylamines 4. The reaction proceeds at 0 degrees C with variable degrees of diastereoselectivity, from moderate to good, mainly depending on the organomagnesium reagent used. The usefulness of compounds 4 has been exemplified with the synthesis of pyrroloazepine 12 through a ring closing metathesis key step.
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33
Total citations:
33
Citations from 2024:
1
(3.03%)
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GOST
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Bonanni M. et al. Double Addition of Grignard Reagents to N-Glycosyl Nitrones: A New Tool for the Construction of Enantiopure Azaheterocycles // Organic Letters. 2004. Vol. 7. No. 2. pp. 319-322.
GOST all authors (up to 50)
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Bonanni M., Marradi M., Cicchi S., Faggi C., Goti A. Double Addition of Grignard Reagents to N-Glycosyl Nitrones: A New Tool for the Construction of Enantiopure Azaheterocycles // Organic Letters. 2004. Vol. 7. No. 2. pp. 319-322.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ol047691e
UR - https://doi.org/10.1021/ol047691e
TI - Double Addition of Grignard Reagents to N-Glycosyl Nitrones: A New Tool for the Construction of Enantiopure Azaheterocycles
T2 - Organic Letters
AU - Bonanni, Marco
AU - Marradi, Marco
AU - Cicchi, Stefano
AU - Faggi, Cristina
AU - Goti, A.
PY - 2004
DA - 2004/12/29
PB - American Chemical Society (ACS)
SP - 319-322
IS - 2
VL - 7
PMID - 15646987
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2004_Bonanni,
author = {Marco Bonanni and Marco Marradi and Stefano Cicchi and Cristina Faggi and A. Goti},
title = {Double Addition of Grignard Reagents to N-Glycosyl Nitrones: A New Tool for the Construction of Enantiopure Azaheterocycles},
journal = {Organic Letters},
year = {2004},
volume = {7},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/ol047691e},
number = {2},
pages = {319--322},
doi = {10.1021/ol047691e}
}
Cite this
MLA
Copy
Bonanni, Marco, et al. “Double Addition of Grignard Reagents to N-Glycosyl Nitrones: A New Tool for the Construction of Enantiopure Azaheterocycles.” Organic Letters, vol. 7, no. 2, Dec. 2004, pp. 319-322. https://doi.org/10.1021/ol047691e.