Borinic Acid/Halide Co-catalyzed Semipinacol Rearrangements of 2,3-Epoxy Alcohols
Publication type: Journal Article
Publication date: 2018-08-15
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
30110171
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A new mode of catalysis of the semipinacol rearrangement of 2,3-epoxy alcohols is described. In combination with a halide salt additive, diarylborinic acids promote a Type II rearrangement that occurs with net retention of configuration. This unusual stereochemical outcome is consistent with a mechanism involving regioselective ring opening of the epoxy alcohol by halide, followed by rearrangement of the resulting halohydrin-derived borinic ester. The protocol is applicable to a range of substrates, enabling ring contractions and expansions as well as stereospecific syntheses of acyclic β-hydroxycarbonyl compounds.
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Total citations:
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Citations from 2025:
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(8.7%)
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Tanveer K., Kim S. J., Taylor M. S. Borinic Acid/Halide Co-catalyzed Semipinacol Rearrangements of 2,3-Epoxy Alcohols // Organic Letters. 2018. Vol. 20. No. 17. pp. 5327-5331.
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Tanveer K., Kim S. J., Taylor M. S. Borinic Acid/Halide Co-catalyzed Semipinacol Rearrangements of 2,3-Epoxy Alcohols // Organic Letters. 2018. Vol. 20. No. 17. pp. 5327-5331.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.8b02248
UR - https://doi.org/10.1021/acs.orglett.8b02248
TI - Borinic Acid/Halide Co-catalyzed Semipinacol Rearrangements of 2,3-Epoxy Alcohols
T2 - Organic Letters
AU - Tanveer, Kashif
AU - Kim, Seung Joon
AU - Taylor, Mark S.
PY - 2018
DA - 2018/08/15
PB - American Chemical Society (ACS)
SP - 5327-5331
IS - 17
VL - 20
PMID - 30110171
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2018_Tanveer,
author = {Kashif Tanveer and Seung Joon Kim and Mark S. Taylor},
title = {Borinic Acid/Halide Co-catalyzed Semipinacol Rearrangements of 2,3-Epoxy Alcohols},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.orglett.8b02248},
number = {17},
pages = {5327--5331},
doi = {10.1021/acs.orglett.8b02248}
}
Cite this
MLA
Copy
Tanveer, Kashif, et al. “Borinic Acid/Halide Co-catalyzed Semipinacol Rearrangements of 2,3-Epoxy Alcohols.” Organic Letters, vol. 20, no. 17, Aug. 2018, pp. 5327-5331. https://doi.org/10.1021/acs.orglett.8b02248.