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Synthesis of dihydrobenzofurans with quaternary carbon center under mild and neutral conditions.
Org Lett. 2013 Sep 06; 15(17):4382-5.OL

Abstract

A new method has been developed for the construction of dihydrobenzofurans from O-aryloxime ethers bearing an α-cyano group using a sequential regioselective isomerization/[3,3]-sigmatropic rearrangement/cyclization reaction in MeOH without any catalysts under neutral conditions at ambient temperature. The current transformation provides environmentally benign and atom-economical access to a variety of dihydrobenzofurans containing a quaternary carbon from readily available cyclic and acyclic oxime ethers.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Takeda N
Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
Ueda M
No affiliation info available
Kagehira S
No affiliation info available
Komei H
No affiliation info available
Tohnai N
No affiliation info available
Miyata M
No affiliation info available
Naito T
No affiliation info available
Miyata O
No affiliation info available

MeSH

BenzofuransCatalysisCyclizationEthersMolecular StructureNitrilesOximes

Pub Type(s)

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

Language

eng

PubMed ID

23957653

Citation

Takeda, Norihiko, et al. "Synthesis of Dihydrobenzofurans With Quaternary Carbon Center Under Mild and Neutral Conditions." Organic Letters, vol. 15, no. 17, 2013, pp. 4382-5.
Takeda N, Ueda M, Kagehira S, et al. Synthesis of dihydrobenzofurans with quaternary carbon center under mild and neutral conditions. Org Lett. 2013;15(17):4382-5.
Takeda, N., Ueda, M., Kagehira, S., Komei, H., Tohnai, N., Miyata, M., Naito, T., & Miyata, O. (2013). Synthesis of dihydrobenzofurans with quaternary carbon center under mild and neutral conditions. Organic Letters, 15(17), 4382-5. https://doi.org/10.1021/ol401897u
Takeda N, et al. Synthesis of Dihydrobenzofurans With Quaternary Carbon Center Under Mild and Neutral Conditions. Org Lett. 2013 Sep 6;15(17):4382-5. PubMed PMID: 23957653.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of dihydrobenzofurans with quaternary carbon center under mild and neutral conditions. AU - Takeda,Norihiko, AU - Ueda,Masafumi, AU - Kagehira,Syunsuke, AU - Komei,Hiroyuki, AU - Tohnai,Norimitsu, AU - Miyata,Mikiji, AU - Naito,Takeaki, AU - Miyata,Okiko, Y1 - 2013/08/19/ PY - 2013/8/21/entrez PY - 2013/8/21/pubmed PY - 2014/2/14/medline SP - 4382 EP - 5 JF - Organic letters JO - Org Lett VL - 15 IS - 17 N2 - A new method has been developed for the construction of dihydrobenzofurans from O-aryloxime ethers bearing an α-cyano group using a sequential regioselective isomerization/[3,3]-sigmatropic rearrangement/cyclization reaction in MeOH without any catalysts under neutral conditions at ambient temperature. The current transformation provides environmentally benign and atom-economical access to a variety of dihydrobenzofurans containing a quaternary carbon from readily available cyclic and acyclic oxime ethers. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23957653/Synthesis_of_dihydrobenzofurans_with_quaternary_carbon_center_under_mild_and_neutral_conditions_ L2 - https://doi.org/10.1021/ol401897u DB - PRIME DP - Unbound Medicine ER -