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Combining Organocatalyzed Aldolization and Reductive Amination: An Efficient Reaction Sequence for the Synthesis of Iminosugars

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2021
Combining_Organocatalyzed_Aldolization_acc_2021.pdf (2.124Mb)
Authors
Ferjančić, Zorana
Saičić, Radomir
Article (Accepted Version)
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Abstract
Over the past two decades, organocatalytic aldol reaction emerged as a powerful method for the enantioselective carbon–carbon bond formation, often offering more efficient, economical and environmentally friendly synthesis of chiral molecules. On the other hand, reductive amination is one of the most important reactions in synthesis of biologically active compounds and drug candidates. Coupling these two reactions results in a powerful combination that allows for a rapid, stereoselective access to substituted, highly functionalized five- and six-membered N-heterocycles. This minireview illustrates the applicability of this approach as the key feature in syntheses of various iminosugars – a class of polyhydroxylated alkaloids with a range of interesting biological activities and high pharmacological potential.
Keywords:
Aldol reaction / Asymmetric synthesis / Iminosugars / Organocatalysis / Reductive amination
Source:
European Journal of Organic Chemistry, 2021, 2021, 22, 3241-3250
Publisher:
  • Wiley
Funding / projects:
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200168 (University of Belgrade, Faculty of Chemistry) (RS-200168)
  • Serbian Academyof Sciences and Arts, Project No F193.
Note:
  • This is the peer-reviewed version of the article: Ferjancic, Z.; Saicic, R. N. Combining Organocatalyzed Aldolization and Reductive Amination: An Efficient Reaction Sequence for the Synthesis of Iminosugars. European Journal of Organic Chemistry 2021, 2021 (22), 3241–3250. https://doi.org/10.1002/ejoc.202100398.
Related info:
  • Version of
    https://doi.org/10.1002/ejoc.202100398

DOI: 10.1002/ejoc.202100398

ISSN: 1434-193X

WoS: 000664610800012

Scopus: 2-s2.0-85108284643
[ Google Scholar ]
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URI
https://cherry.chem.bg.ac.rs/handle/123456789/4577
Collections
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4577
AB  - Over the past two decades, organocatalytic aldol reaction emerged as a powerful method for the enantioselective carbon–carbon bond formation, often offering more efficient, economical and environmentally friendly synthesis of chiral molecules. On the other hand, reductive amination is one of the most important reactions in synthesis of biologically active compounds and drug candidates. Coupling these two reactions results in a powerful combination that allows for a rapid, stereoselective access to substituted, highly functionalized five- and six-membered N-heterocycles. This minireview illustrates the applicability of this approach as the key feature in syntheses of various iminosugars – a class of polyhydroxylated alkaloids with a range of interesting biological activities and high pharmacological potential.
PB  - Wiley
T2  - European Journal of Organic Chemistry
T1  - Combining Organocatalyzed Aldolization and Reductive Amination: An Efficient Reaction Sequence for the Synthesis of Iminosugars
VL  - 2021
IS  - 22
SP  - 3241
EP  - 3250
DO  - 10.1002/ejoc.202100398
ER  - 
@article{
author = "Ferjančić, Zorana and Saičić, Radomir",
year = "2021",
abstract = "Over the past two decades, organocatalytic aldol reaction emerged as a powerful method for the enantioselective carbon–carbon bond formation, often offering more efficient, economical and environmentally friendly synthesis of chiral molecules. On the other hand, reductive amination is one of the most important reactions in synthesis of biologically active compounds and drug candidates. Coupling these two reactions results in a powerful combination that allows for a rapid, stereoselective access to substituted, highly functionalized five- and six-membered N-heterocycles. This minireview illustrates the applicability of this approach as the key feature in syntheses of various iminosugars – a class of polyhydroxylated alkaloids with a range of interesting biological activities and high pharmacological potential.",
publisher = "Wiley",
journal = "European Journal of Organic Chemistry",
title = "Combining Organocatalyzed Aldolization and Reductive Amination: An Efficient Reaction Sequence for the Synthesis of Iminosugars",
volume = "2021",
number = "22",
pages = "3241-3250",
doi = "10.1002/ejoc.202100398"
}
Ferjančić, Z.,& Saičić, R.. (2021). Combining Organocatalyzed Aldolization and Reductive Amination: An Efficient Reaction Sequence for the Synthesis of Iminosugars. in European Journal of Organic Chemistry
Wiley., 2021(22), 3241-3250.
https://doi.org/10.1002/ejoc.202100398
Ferjančić Z, Saičić R. Combining Organocatalyzed Aldolization and Reductive Amination: An Efficient Reaction Sequence for the Synthesis of Iminosugars. in European Journal of Organic Chemistry. 2021;2021(22):3241-3250.
doi:10.1002/ejoc.202100398 .
Ferjančić, Zorana, Saičić, Radomir, "Combining Organocatalyzed Aldolization and Reductive Amination: An Efficient Reaction Sequence for the Synthesis of Iminosugars" in European Journal of Organic Chemistry, 2021, no. 22 (2021):3241-3250,
https://doi.org/10.1002/ejoc.202100398 . .

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