Faculty of Chemistry Repository - Cherry
University of Belgrade - Faculty of Chemistry
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrillic)
    • Serbian (Latin)
  • Login
View Item 
  •   Cherry
  • Hemijski fakultet
  • Publikacije
  • View Item
  •   Cherry
  • Hemijski fakultet
  • Publikacije
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes

Authorized Users Only
2017
Authors
Marjanović-Trajković, Jasna
Milanović, Vesna D.
Ferjančić, Zorana
Saičić, Radomir
Article (Published version)
Metadata
Show full item record
Abstract
Reagent stereocontrol in the proline-catalyzed aldol reaction of 2,2-dimethyl-1,3-dioxane-5-one 1 with chiral aldehydes has been investigated. Synthetically useful levels of diastereoselectivity could be achieved in reactions with acyclic chiral alpha-oxy and alpha-amino aldehydes in both matched and mismatched cases. By using this reaction as a key step, two medicinally relevant azasugars, 1-deoxy-galactonojirimycin (9) and 2,5-dideoxy-2,5-imino-d-altritol (10), were efficiently synthesized.
Keywords:
Synthetic methods / Organocatalysis / Aldol reactions / Iminosugars / Diastereoselectivity
Source:
European Journal of Organic Chemistry, 2017, 41, 6146-6153
Publisher:
  • Wiley-V C H Verlag Gmbh, Weinheim
Funding / projects:
  • The development of new synthetic methods and their application in the synthesis of natural products and biologically active molecules (RS-172027)
  • Serbian Academy of Sciences and Arts [F193]
Note:
  • Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3229

DOI: 10.1002/ejoc.201701073

ISSN: 1434-193X

WoS: 000414849900007

Scopus: 2-s2.0-85033474381
[ Google Scholar ]
8
5
URI
https://cherry.chem.bg.ac.rs/handle/123456789/2410
Collections
  • Publikacije
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Marjanović-Trajković, Jasna
AU  - Milanović, Vesna D.
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2410
AB  - Reagent stereocontrol in the proline-catalyzed aldol reaction of 2,2-dimethyl-1,3-dioxane-5-one 1 with chiral aldehydes has been investigated. Synthetically useful levels of diastereoselectivity could be achieved in reactions with acyclic chiral alpha-oxy and alpha-amino aldehydes in both matched and mismatched cases. By using this reaction as a key step, two medicinally relevant azasugars, 1-deoxy-galactonojirimycin (9) and 2,5-dideoxy-2,5-imino-d-altritol (10), were efficiently synthesized.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes
IS  - 41
SP  - 6146
EP  - 6153
DO  - 10.1002/ejoc.201701073
UR  - Kon_3226
ER  - 
@article{
author = "Marjanović-Trajković, Jasna and Milanović, Vesna D. and Ferjančić, Zorana and Saičić, Radomir",
year = "2017",
abstract = "Reagent stereocontrol in the proline-catalyzed aldol reaction of 2,2-dimethyl-1,3-dioxane-5-one 1 with chiral aldehydes has been investigated. Synthetically useful levels of diastereoselectivity could be achieved in reactions with acyclic chiral alpha-oxy and alpha-amino aldehydes in both matched and mismatched cases. By using this reaction as a key step, two medicinally relevant azasugars, 1-deoxy-galactonojirimycin (9) and 2,5-dideoxy-2,5-imino-d-altritol (10), were efficiently synthesized.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes",
number = "41",
pages = "6146-6153",
doi = "10.1002/ejoc.201701073",
url = "Kon_3226"
}
Marjanović-Trajković, J., Milanović, V. D., Ferjančić, Z.,& Saičić, R.. (2017). On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(41), 6146-6153.
https://doi.org/10.1002/ejoc.201701073
Kon_3226
Marjanović-Trajković J, Milanović VD, Ferjančić Z, Saičić R. On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes. in European Journal of Organic Chemistry. 2017;(41):6146-6153.
doi:10.1002/ejoc.201701073
Kon_3226 .
Marjanović-Trajković, Jasna, Milanović, Vesna D., Ferjančić, Zorana, Saičić, Radomir, "On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes" in European Journal of Organic Chemistry, no. 41 (2017):6146-6153,
https://doi.org/10.1002/ejoc.201701073 .,
Kon_3226 .

DSpace software copyright © 2002-2015  DuraSpace
About CHERRY - CHEmistry RepositoRY | Send Feedback

re3dataOpenAIRERCUB
 

 

All of DSpaceInstitutions/communitiesAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CHERRY - CHEmistry RepositoRY | Send Feedback

re3dataOpenAIRERCUB