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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
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.
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 .
