Application of Iridium Catalized Allylic Substitution Reactions in the Synthesis of Branched Triptamines and Homologues via Tandem Hydroformylation/Fischer Indole Synthesis
Само за регистроване кориснике
2008
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Combination of enantioselective allylation reactions with a tandem hydroformylation–Fischer indole synthesis sequence as a highly diversity-oriented strategy for the synthesis of tryptamines and homologues was explored. This modular approach allows the substituents at C3 of the indole core, the type of the amine moiety, and the distance of the amine moiety to the indole core in the final synthetic step to be defined. The starting materials required for the hydroformylation step were synthesized viairidium catalyzed enantioselective allylic substitution reactions in high yields and excellent enantioselectivities. The Rh catalyzed hydroformylation step in the presence of phenyl hydrazine, allows the in situ formed aldehyde to be trapped as the hydrazone. Subsequent acid catalyzed indolization furnishes the desired indole structures in moderate to good yields.
Кључне речи:
tandem / hydroformylation / Fischer indole synthesis / tryptamines / allylation / catalysisИзвор:
Organic and Biomolecular Chemistry, 2008, 6, 3723-3731Издавач:
- Royal Society of Chemistry
DOI: 10.1039/B809143A
ISSN: 1477-0520
PubMed: 18843402
Scopus: 2-s2.0-53549123254
Институција/група
IHTMTY - JOUR AU - Bondžić, Bojan AU - Farwick, Andreas AU - Liebich, Jens AU - Eilbracht, Peter PY - 2008 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/6807 AB - Combination of enantioselective allylation reactions with a tandem hydroformylation–Fischer indole synthesis sequence as a highly diversity-oriented strategy for the synthesis of tryptamines and homologues was explored. This modular approach allows the substituents at C3 of the indole core, the type of the amine moiety, and the distance of the amine moiety to the indole core in the final synthetic step to be defined. The starting materials required for the hydroformylation step were synthesized viairidium catalyzed enantioselective allylic substitution reactions in high yields and excellent enantioselectivities. The Rh catalyzed hydroformylation step in the presence of phenyl hydrazine, allows the in situ formed aldehyde to be trapped as the hydrazone. Subsequent acid catalyzed indolization furnishes the desired indole structures in moderate to good yields. PB - Royal Society of Chemistry T2 - Organic and Biomolecular Chemistry T1 - Application of Iridium Catalized Allylic Substitution Reactions in the Synthesis of Branched Triptamines and Homologues via Tandem Hydroformylation/Fischer Indole Synthesis VL - 6 SP - 3723 EP - 3731 DO - 10.1039/B809143A ER -
@article{ author = "Bondžić, Bojan and Farwick, Andreas and Liebich, Jens and Eilbracht, Peter", year = "2008", abstract = "Combination of enantioselective allylation reactions with a tandem hydroformylation–Fischer indole synthesis sequence as a highly diversity-oriented strategy for the synthesis of tryptamines and homologues was explored. This modular approach allows the substituents at C3 of the indole core, the type of the amine moiety, and the distance of the amine moiety to the indole core in the final synthetic step to be defined. The starting materials required for the hydroformylation step were synthesized viairidium catalyzed enantioselective allylic substitution reactions in high yields and excellent enantioselectivities. The Rh catalyzed hydroformylation step in the presence of phenyl hydrazine, allows the in situ formed aldehyde to be trapped as the hydrazone. Subsequent acid catalyzed indolization furnishes the desired indole structures in moderate to good yields.", publisher = "Royal Society of Chemistry", journal = "Organic and Biomolecular Chemistry", title = "Application of Iridium Catalized Allylic Substitution Reactions in the Synthesis of Branched Triptamines and Homologues via Tandem Hydroformylation/Fischer Indole Synthesis", volume = "6", pages = "3723-3731", doi = "10.1039/B809143A" }
Bondžić, B., Farwick, A., Liebich, J.,& Eilbracht, P.. (2008). Application of Iridium Catalized Allylic Substitution Reactions in the Synthesis of Branched Triptamines and Homologues via Tandem Hydroformylation/Fischer Indole Synthesis. in Organic and Biomolecular Chemistry Royal Society of Chemistry., 6, 3723-3731. https://doi.org/10.1039/B809143A
Bondžić B, Farwick A, Liebich J, Eilbracht P. Application of Iridium Catalized Allylic Substitution Reactions in the Synthesis of Branched Triptamines and Homologues via Tandem Hydroformylation/Fischer Indole Synthesis. in Organic and Biomolecular Chemistry. 2008;6:3723-3731. doi:10.1039/B809143A .
Bondžić, Bojan, Farwick, Andreas, Liebich, Jens, Eilbracht, Peter, "Application of Iridium Catalized Allylic Substitution Reactions in the Synthesis of Branched Triptamines and Homologues via Tandem Hydroformylation/Fischer Indole Synthesis" in Organic and Biomolecular Chemistry, 6 (2008):3723-3731, https://doi.org/10.1039/B809143A . .