Enantioselective Protonation of Silyl Enol Ether Using Excited State Proton Transfer Dyes
Publication type: Journal Article
Publication date: 2016-10-10
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
27718586
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Enantiopure excited state proton transfer (ESPT) dyes were used for the asymmetric protonation of silyl enol ether. Under 365 nm irradiation, with 3,3'-dibromo-VANOL as the ESPT dye, up to 49% enantioselectivity with a 68% yield of product was observed at room temperature. The reaction is effective with a range of silyl enol ethers and can also be achieved with visible light upon the addition of triplet sensitizer. The relatively low ee of the protonated product is due to the racemization/decomposition of the ESPT dye in the excited state as indicated by circular dichroism, HPLC, and UV-vis spectroscopy.
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GOST
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Das A. K., Ayad S., Hanson K. M. Enantioselective Protonation of Silyl Enol Ether Using Excited State Proton Transfer Dyes // Organic Letters. 2016. Vol. 18. No. 20. pp. 5416-5419.
GOST all authors (up to 50)
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Das A. K., Ayad S., Hanson K. M. Enantioselective Protonation of Silyl Enol Ether Using Excited State Proton Transfer Dyes // Organic Letters. 2016. Vol. 18. No. 20. pp. 5416-5419.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.6b02820
UR - https://doi.org/10.1021/acs.orglett.6b02820
TI - Enantioselective Protonation of Silyl Enol Ether Using Excited State Proton Transfer Dyes
T2 - Organic Letters
AU - Das, Anjan Kumar
AU - Ayad, Suliman
AU - Hanson, Kenneth M.
PY - 2016
DA - 2016/10/10
PB - American Chemical Society (ACS)
SP - 5416-5419
IS - 20
VL - 18
PMID - 27718586
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2016_Das,
author = {Anjan Kumar Das and Suliman Ayad and Kenneth M. Hanson},
title = {Enantioselective Protonation of Silyl Enol Ether Using Excited State Proton Transfer Dyes},
journal = {Organic Letters},
year = {2016},
volume = {18},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.orglett.6b02820},
number = {20},
pages = {5416--5419},
doi = {10.1021/acs.orglett.6b02820}
}
Cite this
MLA
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Das, Anjan Kumar, et al. “Enantioselective Protonation of Silyl Enol Ether Using Excited State Proton Transfer Dyes.” Organic Letters, vol. 18, no. 20, Oct. 2016, pp. 5416-5419. https://doi.org/10.1021/acs.orglett.6b02820.