Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols
Publication type: Journal Article
Publication date: 2021-10-07
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
34615353
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The silyl-Prins cyclization of geminal vinylsilyl alcohols and aldehydes, promoted by TMSOTf, provides access to polysubstituted tetrahydropyrans in which the silyl group remains in the molecule and an aryl group has migrated from silicon to carbon. This domino silyl-Prins/aryl migration process is general and high-yielding for aryl, vinyl, or alkyl aldehydes. Moreover, cyclization proceeds with very high stereocontrol in a one-pot reaction in which both quaternary and tertiary stereogenic centers have been created.
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16
Total citations:
16
Citations from 2024:
13
(81.25%)
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MLA
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GOST
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Díez Poza C., Barbero A. Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols // Organic Letters. 2021. Vol. 23. No. 21. pp. 8385-8389.
GOST all authors (up to 50)
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Díez Poza C., Barbero A. Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols // Organic Letters. 2021. Vol. 23. No. 21. pp. 8385-8389.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.1c03121
UR - https://doi.org/10.1021/acs.orglett.1c03121
TI - Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols
T2 - Organic Letters
AU - Díez Poza, Carlos
AU - Barbero, Asunción
PY - 2021
DA - 2021/10/07
PB - American Chemical Society (ACS)
SP - 8385-8389
IS - 21
VL - 23
PMID - 34615353
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_Díez Poza,
author = {Carlos Díez Poza and Asunción Barbero},
title = {Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols},
journal = {Organic Letters},
year = {2021},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.orglett.1c03121},
number = {21},
pages = {8385--8389},
doi = {10.1021/acs.orglett.1c03121}
}
Cite this
MLA
Copy
Díez Poza, Carlos, and Asunción Barbero. “Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols.” Organic Letters, vol. 23, no. 21, Oct. 2021, pp. 8385-8389. https://doi.org/10.1021/acs.orglett.1c03121.