Journal of the American Chemical Society, volume 136, issue 25, pages 8911-8914
Redox-Triggered C–C Coupling of Alcohols and Vinyl Epoxides: Diastereo- and Enantioselective Formation of All-Carbon Quaternary Centers via tert-(Hydroxy)-Prenylation
Publication type: Journal Article
Publication date: 2014-06-10
Q1
Q1
SJR: 5.489
CiteScore: 24.4
Impact factor: 14.4
ISSN: 00027863, 15205126
PubMed ID:
24915473
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Iridium catalyzed primary alcohol oxidation triggers reductive C–O bond cleavage of isoprene oxide to form aldehyde-allyliridium pairs that combine to form products of tert-(hydroxy)-prenylation, a motif found in >2000 terpenoid natural products. Curtin–Hammett effects are exploited to enforce high levels of anti-diastereo- and enantioselectivity in the formation of an all-carbon quaternary center. The present redox-triggered carbonyl additions occur in the absence of stoichiometric byproducts, premetalated reagents, and discrete alcohol-to-aldehyde redox manipulations.
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Feng J., Garza V. J., Krische M. J. Redox-Triggered C–C Coupling of Alcohols and Vinyl Epoxides: Diastereo- and Enantioselective Formation of All-Carbon Quaternary Centers via tert-(Hydroxy)-Prenylation // Journal of the American Chemical Society. 2014. Vol. 136. No. 25. pp. 8911-8914.
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Feng J., Garza V. J., Krische M. J. Redox-Triggered C–C Coupling of Alcohols and Vinyl Epoxides: Diastereo- and Enantioselective Formation of All-Carbon Quaternary Centers via tert-(Hydroxy)-Prenylation // Journal of the American Chemical Society. 2014. Vol. 136. No. 25. pp. 8911-8914.
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TY - JOUR
DO - 10.1021/ja504625m
UR - https://doi.org/10.1021/ja504625m
TI - Redox-Triggered C–C Coupling of Alcohols and Vinyl Epoxides: Diastereo- and Enantioselective Formation of All-Carbon Quaternary Centers via tert-(Hydroxy)-Prenylation
T2 - Journal of the American Chemical Society
AU - Feng, Jiajie
AU - Garza, Victoria J
AU - Krische, Michael J
PY - 2014
DA - 2014/06/10
PB - American Chemical Society (ACS)
SP - 8911-8914
IS - 25
VL - 136
PMID - 24915473
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2014_Feng,
author = {Jiajie Feng and Victoria J Garza and Michael J Krische},
title = {Redox-Triggered C–C Coupling of Alcohols and Vinyl Epoxides: Diastereo- and Enantioselective Formation of All-Carbon Quaternary Centers via tert-(Hydroxy)-Prenylation},
journal = {Journal of the American Chemical Society},
year = {2014},
volume = {136},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/ja504625m},
number = {25},
pages = {8911--8914},
doi = {10.1021/ja504625m}
}
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Feng, Jiajie, et al. “Redox-Triggered C–C Coupling of Alcohols and Vinyl Epoxides: Diastereo- and Enantioselective Formation of All-Carbon Quaternary Centers via tert-(Hydroxy)-Prenylation.” Journal of the American Chemical Society, vol. 136, no. 25, Jun. 2014, pp. 8911-8914. https://doi.org/10.1021/ja504625m.