Combining Organocatalyzed Aldolization and Reductive Amination: An Efficient Reaction Sequence for the Synthesis of Iminosugars
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 aminationSource:
European Journal of Organic Chemistry, 2021, 2021, 22, 3241-3250Publisher:
- Wiley
Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200168 (University of Belgrade, Faculty of Chemistry) (RS-MESTD-inst-2020-200168)
- Serbian Academyof Sciences and Arts, Project No F193.
Note:
- Peer-reviewed manuscript: https://cherry.chem.bg.ac.rs/handle/123456789/4577
DOI: 10.1002/ejoc.202100398
ISSN: 1434-193X
WoS: 000664610800012
Scopus: 2-s2.0-85108284643
URI
https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.202100398https://cherry.chem.bg.ac.rs/handle/123456789/4576
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Ferjančić, Zorana AU - Saičić, Radomir PY - 2021 UR - https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.202100398 UR - https://cherry.chem.bg.ac.rs/handle/123456789/4576 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 . .