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Iron-catalysed asymmetric tandem spiro-cyclization using dioxygen in air as the hydrogen acceptor.
Chem Commun (Camb). 2014 May 21; 50(39):5053-6.CC

Abstract

A tandem combination of ortho-quinone methide (o-QM) formation/Michael addition/asymmetric dearomatization, which is catalysed by an iron-salan complex in air with high enantioselectivity, provides an efficient method for spirocyclic (2H)-dihydrobenzofuran synthesis from 2-naphthols and phenols. The key to the success of the tandem synthesis is the development of aerobic oxidative o-QM formation.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Oguma T
Department of Chemistry, Graduate School of Science, Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan.
Katsuki T
No affiliation info available

MeSH

AirCatalysisCyclizationHydrogenIndolequinonesIronMolecular StructureNaphtholsOxidation-ReductionOxygenPhenolsSpiro CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24715032

Citation

Oguma, Takuya, and Tsutomu Katsuki. "Iron-catalysed Asymmetric Tandem Spiro-cyclization Using Dioxygen in Air as the Hydrogen Acceptor." Chemical Communications (Cambridge, England), vol. 50, no. 39, 2014, pp. 5053-6.
Oguma T, Katsuki T. Iron-catalysed asymmetric tandem spiro-cyclization using dioxygen in air as the hydrogen acceptor. Chem Commun (Camb). 2014;50(39):5053-6.
Oguma, T., & Katsuki, T. (2014). Iron-catalysed asymmetric tandem spiro-cyclization using dioxygen in air as the hydrogen acceptor. Chemical Communications (Cambridge, England), 50(39), 5053-6. https://doi.org/10.1039/c4cc01555j
Oguma T, Katsuki T. Iron-catalysed Asymmetric Tandem Spiro-cyclization Using Dioxygen in Air as the Hydrogen Acceptor. Chem Commun (Camb). 2014 May 21;50(39):5053-6. PubMed PMID: 24715032.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Iron-catalysed asymmetric tandem spiro-cyclization using dioxygen in air as the hydrogen acceptor. AU - Oguma,Takuya, AU - Katsuki,Tsutomu, Y1 - 2014/04/09/ PY - 2014/4/10/entrez PY - 2014/4/10/pubmed PY - 2015/4/15/medline SP - 5053 EP - 6 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) VL - 50 IS - 39 N2 - A tandem combination of ortho-quinone methide (o-QM) formation/Michael addition/asymmetric dearomatization, which is catalysed by an iron-salan complex in air with high enantioselectivity, provides an efficient method for spirocyclic (2H)-dihydrobenzofuran synthesis from 2-naphthols and phenols. The key to the success of the tandem synthesis is the development of aerobic oxidative o-QM formation. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/24715032/Iron_catalysed_asymmetric_tandem_spiro_cyclization_using_dioxygen_in_air_as_the_hydrogen_acceptor_ DB - PRIME DP - Unbound Medicine ER -