Electrochemically deprotonated chiral nickel(II) glycinate in stereoselective nucleophilic addition to michael acceptors: Advantages and limitations
Oleg A Levitskiy
1
,
Yuri Grishin
1
,
Yuri K. Grishin
1
,
Asmik A Ambartsumyan
2
,
Andrei V. Churakov
3, 4
,
Konstantin K Babievsky
2
,
Publication type: Journal Article
Publication date: 2014-05-06
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
A Ni(II) glycine/Schiff base complex containing (S)-o-[N-(N-benzylprolyl)amino]benzophenone as an auxiliary chiral moiety was deprotonated using electrochemically generated azobenzene radical anion and used in nucleophilic addition to Michael acceptors, terminal 2,2- and 1,2-disubstituted alkenes ((2E)-1,3-diphenylprop-2-en-1-one, (E)-2-nitroethenylbenzene, 2-methylprop-2-enenitrile, Ni(II) dehydroalanine complex), creating a preparatively convenient path for asymmetric functionalization of the α-glycine carbon in the Ni(II) coordination environment, yielding new chiral Ni(II) complexes. The main advantage of the application of electrochemical techniques is the possibility of precise control of the concentration of a base and its in situ reaction with the complex. This opens up the possibility to carry out further functionalization of the anionic adduct formed in Michael addition via a successive one-pot reaction with the other electrophile. A one-pot cascade reaction of electrochemically deprotonated Ni(...
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Magdesieva T. V. et al. Electrochemically deprotonated chiral nickel(II) glycinate in stereoselective nucleophilic addition to michael acceptors: Advantages and limitations // Organometallics. 2014. Vol. 33. No. 18. pp. 4629-4638.
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Magdesieva T. V., Levitskiy O. A., Grishin Y., Grishin Y. K., Ambartsumyan A. A., Kiskin M. A., Churakov A. V., Babievsky K. K., Kochetkov K. A. Electrochemically deprotonated chiral nickel(II) glycinate in stereoselective nucleophilic addition to michael acceptors: Advantages and limitations // Organometallics. 2014. Vol. 33. No. 18. pp. 4629-4638.
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TY - JOUR
DO - 10.1021/om500070n
UR - https://pubs.acs.org/doi/10.1021/om500070n
TI - Electrochemically deprotonated chiral nickel(II) glycinate in stereoselective nucleophilic addition to michael acceptors: Advantages and limitations
T2 - Organometallics
AU - Magdesieva, Tatiana V.
AU - Levitskiy, Oleg A
AU - Grishin, Yuri
AU - Grishin, Yuri K.
AU - Ambartsumyan, Asmik A
AU - Kiskin, Mikhail A.
AU - Churakov, Andrei V.
AU - Babievsky, Konstantin K
AU - Kochetkov, Konstantin A.
PY - 2014
DA - 2014/05/06
PB - American Chemical Society (ACS)
SP - 4629-4638
IS - 18
VL - 33
SN - 0276-7333
SN - 1520-6041
ER -
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BibTex (up to 50 authors)
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@article{2014_Magdesieva,
author = {Tatiana V. Magdesieva and Oleg A Levitskiy and Yuri Grishin and Yuri K. Grishin and Asmik A Ambartsumyan and Mikhail A. Kiskin and Andrei V. Churakov and Konstantin K Babievsky and Konstantin A. Kochetkov},
title = {Electrochemically deprotonated chiral nickel(II) glycinate in stereoselective nucleophilic addition to michael acceptors: Advantages and limitations},
journal = {Organometallics},
year = {2014},
volume = {33},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://pubs.acs.org/doi/10.1021/om500070n},
number = {18},
pages = {4629--4638},
doi = {10.1021/om500070n}
}
Cite this
MLA
Copy
Magdesieva, Tatiana V., et al. “Electrochemically deprotonated chiral nickel(II) glycinate in stereoselective nucleophilic addition to michael acceptors: Advantages and limitations.” Organometallics, vol. 33, no. 18, May. 2014, pp. 4629-4638. https://pubs.acs.org/doi/10.1021/om500070n.
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