Synthesis of non-racemic dihydrofurans via Ni(II)-catalyzed asymmetric Michael addition
Dmitry S Nikerov
1
,
M A Ashatkina
1
,
Vadim Shiryaev
1
,
Ilya M Tkachenko
1
,
A N Reznikov
1
,
Yuri Klimochkin
1
Publication type: Journal Article
Publication date: 2021-03-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A highly efficient strategy for the enantio- and diastereoselective synthesis of 4,5-dihydrofuran derivatives was developed. Addition of carbonyl compounds which contain bulky adamantyl substituent and β-keto or phosphonate group to conjugated α-bromonitroolefins in the presence of a chiral Ni(II) complex gave corresponding non-racemic products of Michael reaction. These adducts were used for intramolecular cyclization leading to trans-4,5-dihydrofurans with two stereocenters. Resulting trans-4,5-dihydrofurans were obtained in good yields with moderate to high enantioselectivities (84–99% ee) and excellent diastereoselectivities (dr >99%).
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Total citations:
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GOST
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Nikerov D. S. et al. Synthesis of non-racemic dihydrofurans via Ni(II)-catalyzed asymmetric Michael addition // Tetrahedron. 2021. Vol. 84. p. 132029.
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Nikerov D. S., Ashatkina M. A., Shiryaev V., Tkachenko I. M., Rybakov V. B., Reznikov A. N., Klimochkin Y. Synthesis of non-racemic dihydrofurans via Ni(II)-catalyzed asymmetric Michael addition // Tetrahedron. 2021. Vol. 84. p. 132029.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.tet.2021.132029
UR - https://doi.org/10.1016/j.tet.2021.132029
TI - Synthesis of non-racemic dihydrofurans via Ni(II)-catalyzed asymmetric Michael addition
T2 - Tetrahedron
AU - Nikerov, Dmitry S
AU - Ashatkina, M A
AU - Shiryaev, Vadim
AU - Tkachenko, Ilya M
AU - Rybakov, Victor B.
AU - Reznikov, A N
AU - Klimochkin, Yuri
PY - 2021
DA - 2021/03/01
PB - Elsevier
SP - 132029
VL - 84
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2021_Nikerov,
author = {Dmitry S Nikerov and M A Ashatkina and Vadim Shiryaev and Ilya M Tkachenko and Victor B. Rybakov and A N Reznikov and Yuri Klimochkin},
title = {Synthesis of non-racemic dihydrofurans via Ni(II)-catalyzed asymmetric Michael addition},
journal = {Tetrahedron},
year = {2021},
volume = {84},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/j.tet.2021.132029},
pages = {132029},
doi = {10.1016/j.tet.2021.132029}
}