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
Само за регистроване кориснике
2017
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
Synthetic methods / Organocatalysis / Aldol reactions / Iminosugars / DiastereoselectivityИзвор:
European Journal of Organic Chemistry, 2017, 41, 6146-6153Издавач:
- Wiley-V C H Verlag Gmbh, Weinheim
Финансирање / пројекти:
- Развој нових синтетичких метода и њихова примена у синтези природних производа и биолошки активних једињења (RS-MESTD-Basic Research (BR or ON)-172027)
- Serbian Academy of Sciences and Arts [F193]
Напомена:
- 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
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - 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 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" }
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
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 .
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 . .