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Preparation of enantioenriched γ-substituted lactones via asymmetric transfer hydrogenation of β-azidocyclopropane carboxylates using the Ru-TsDPEN complex.
Org Lett. 2014 Aug 15; 16(16):4204-7.OL

Abstract

The asymmetric transfer hydrogenation of racemic β-azidocyclopropane carboxylates has been explored. Ru-TsDPEN B is found to be a good catalyst for the formation of enantioenriched γ-lactones through a four-step sequence of azide reduction/cyclopropane ring cleavage/ketone transfer hydrogenation/lactonization, and the enantiomeric excess of the lactones was up to 94%.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Su Y
State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University , Lanzhou 730000, China.
Tu YQ
No affiliation info available
Gu P
No affiliation info available

MeSH

Carboxylic AcidsCatalysisEthylenediaminesHydrogenationKetonesLactonesMolecular StructureOrganometallic CompoundsRutheniumStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25083937

Citation

Su, Yan, et al. "Preparation of Enantioenriched Γ-substituted Lactones Via Asymmetric Transfer Hydrogenation of Β-azidocyclopropane Carboxylates Using the Ru-TsDPEN Complex." Organic Letters, vol. 16, no. 16, 2014, pp. 4204-7.
Su Y, Tu YQ, Gu P. Preparation of enantioenriched γ-substituted lactones via asymmetric transfer hydrogenation of β-azidocyclopropane carboxylates using the Ru-TsDPEN complex. Org Lett. 2014;16(16):4204-7.
Su, Y., Tu, Y. Q., & Gu, P. (2014). Preparation of enantioenriched γ-substituted lactones via asymmetric transfer hydrogenation of β-azidocyclopropane carboxylates using the Ru-TsDPEN complex. Organic Letters, 16(16), 4204-7. https://doi.org/10.1021/ol501895k
Su Y, Tu YQ, Gu P. Preparation of Enantioenriched Γ-substituted Lactones Via Asymmetric Transfer Hydrogenation of Β-azidocyclopropane Carboxylates Using the Ru-TsDPEN Complex. Org Lett. 2014 Aug 15;16(16):4204-7. PubMed PMID: 25083937.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Preparation of enantioenriched γ-substituted lactones via asymmetric transfer hydrogenation of β-azidocyclopropane carboxylates using the Ru-TsDPEN complex. AU - Su,Yan, AU - Tu,Yong-Qiang, AU - Gu,Peiming, Y1 - 2014/08/01/ PY - 2014/8/2/entrez PY - 2014/8/2/pubmed PY - 2015/5/23/medline SP - 4204 EP - 7 JF - Organic letters JO - Org Lett VL - 16 IS - 16 N2 - The asymmetric transfer hydrogenation of racemic β-azidocyclopropane carboxylates has been explored. Ru-TsDPEN B is found to be a good catalyst for the formation of enantioenriched γ-lactones through a four-step sequence of azide reduction/cyclopropane ring cleavage/ketone transfer hydrogenation/lactonization, and the enantiomeric excess of the lactones was up to 94%. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25083937/Preparation_of_enantioenriched_γ_substituted_lactones_via_asymmetric_transfer_hydrogenation_of_β_azidocyclopropane_carboxylates_using_the_Ru_TsDPEN_complex_ DB - PRIME DP - Unbound Medicine ER -