Rhodium Catalysts with a Chiral Cyclopentadienyl Ligand Derived from Natural R‐Myrtenal
Publication type: Journal Article
Publication date: 2020-09-15
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A new chiral cyclopentadiene CpmyrH was synthesized from the natural terpene (R)‐myrtenal in 5 steps and about 40 % total yield. The key step was the reaction of vinyl‐dibromocyclopropane derivative with MeLi which provided the diene CpmyrH via Skattebøl rearrangement. The reaction of CpmyrH with [(cod)Rh(OAc)]2 gave the rhodium(I) complex (Cpmyr)Rh(cod) and subsequent oxidation with halogens X2 gave the rhodium(III) complexes [(Cpmyr)RhX2]2 (X = Br, I). Complex (Cpmyr)Rh(cod) in combination with benzoyl peroxide catalyzed the C–H activation of O‐pivaloyl‐phenylhydroxamic acid and its subsequent annulation with alkenes giving dihydroisoquinolones with high yield (70–90 %) but moderate enantioselectivity (16–36 % ee).
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Pototskiy R. A. et al. Rhodium Catalysts with a Chiral Cyclopentadienyl Ligand Derived from Natural R‐Myrtenal // European Journal of Organic Chemistry. 2020. Vol. 2020. No. 37. pp. 6019-6025.
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Pototskiy R. A., Kolos A. V., Nelyubina Y. V., Perekalin D. S. Rhodium Catalysts with a Chiral Cyclopentadienyl Ligand Derived from Natural R‐Myrtenal // European Journal of Organic Chemistry. 2020. Vol. 2020. No. 37. pp. 6019-6025.
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RIS
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TY - JOUR
DO - 10.1002/ejoc.202001029
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202001029
TI - Rhodium Catalysts with a Chiral Cyclopentadienyl Ligand Derived from Natural R‐Myrtenal
T2 - European Journal of Organic Chemistry
AU - Pototskiy, Roman A
AU - Kolos, Andrey V
AU - Nelyubina, Yulia V.
AU - Perekalin, Dmitry S
PY - 2020
DA - 2020/09/15
PB - Wiley
SP - 6019-6025
IS - 37
VL - 2020
SN - 1434-193X
SN - 1099-0690
ER -
Cite this
BibTex (up to 50 authors)
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@article{2020_Pototskiy,
author = {Roman A Pototskiy and Andrey V Kolos and Yulia V. Nelyubina and Dmitry S Perekalin},
title = {Rhodium Catalysts with a Chiral Cyclopentadienyl Ligand Derived from Natural R‐Myrtenal},
journal = {European Journal of Organic Chemistry},
year = {2020},
volume = {2020},
publisher = {Wiley},
month = {sep},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202001029},
number = {37},
pages = {6019--6025},
doi = {10.1002/ejoc.202001029}
}
Cite this
MLA
Copy
Pototskiy, Roman A., et al. “Rhodium Catalysts with a Chiral Cyclopentadienyl Ligand Derived from Natural R‐Myrtenal.” European Journal of Organic Chemistry, vol. 2020, no. 37, Sep. 2020, pp. 6019-6025. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202001029.