Organic Letters, volume 16, issue 24, pages 6468-6471
Catalysis and Chemodivergence in the Interrupted, Formal Homo-Nazarov Cyclization Using Allylsilanes
Publication type: Journal Article
Publication date: 2014-12-11
Journal:
Organic Letters
Q1
Q1
SJR: 1.245
CiteScore: 9.3
Impact factor: 4.9
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A chemodivergent, Lewis acid catalyzed allylsilane interrupted formal homo-Nazarov cyclization is disclosed. With catalytic amounts of SnCl4 and in the presence of allyltrimethylsilane, a formal Hosomi-Sakurai-type allylation of the oxyallyl cation intermediate is observed. A variety of functionalized donor-acceptor cyclopropanes and allylsilanes were shown to be amenable to the reaction transformation and the allyl products were formed in up to 92% yield. Under dilute reaction conditions with stoichiometric SnCl4 and at reduced temperatures, an unusual formal [3 + 2]-cycloaddition between the allylsilane and the oxyallyl cation occurred to give hexahydrobenzofuran products in up to 69% yield.
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Shenje R. et al. Catalysis and Chemodivergence in the Interrupted, Formal Homo-Nazarov Cyclization Using Allylsilanes // Organic Letters. 2014. Vol. 16. No. 24. pp. 6468-6471.
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Shenje R., Williams C. W., Francois K. M., France S. Catalysis and Chemodivergence in the Interrupted, Formal Homo-Nazarov Cyclization Using Allylsilanes // Organic Letters. 2014. Vol. 16. No. 24. pp. 6468-6471.
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TY - JOUR
DO - 10.1021/ol503305r
UR - https://doi.org/10.1021/ol503305r
TI - Catalysis and Chemodivergence in the Interrupted, Formal Homo-Nazarov Cyclization Using Allylsilanes
T2 - Organic Letters
AU - Shenje, Raynold
AU - Williams, Corey W
AU - Francois, Katherine M
AU - France, Stefan
PY - 2014
DA - 2014/12/11
PB - American Chemical Society (ACS)
SP - 6468-6471
IS - 24
VL - 16
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2014_Shenje,
author = {Raynold Shenje and Corey W Williams and Katherine M Francois and Stefan France},
title = {Catalysis and Chemodivergence in the Interrupted, Formal Homo-Nazarov Cyclization Using Allylsilanes},
journal = {Organic Letters},
year = {2014},
volume = {16},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/ol503305r},
number = {24},
pages = {6468--6471},
doi = {10.1021/ol503305r}
}
Cite this
MLA
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Shenje, Raynold, et al. “Catalysis and Chemodivergence in the Interrupted, Formal Homo-Nazarov Cyclization Using Allylsilanes.” Organic Letters, vol. 16, no. 24, Dec. 2014, pp. 6468-6471. https://doi.org/10.1021/ol503305r.