Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine

Rie Fujita; Kengo Hanaya; Takeshi Sugai; Shuhei Higashibayashi

doi:10.1038/s41598-021-03448-9

Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine

Rie Fujita, Kengo Hanaya, Takeshi Sugai, Shuhei Higashibayashi

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

Construction of the hydroquinoline skeleton of symbioimine by Cu-mediated N-alkenylation or O-alkenylation of an allyl aminoalcohol, in which either chemoselectivity could lead to the target compound, was investigated. O-alkenylation followed by Claisen rearrangement was favored with high selectivity under a ligand-free condition. Subsequent intramolecular condensation furnished the hydroquinoline skeleton of symbioimine.

Original language	English
Article number	24078
Journal	Scientific reports
Volume	11
Issue number	1
DOIs	https://doi.org/10.1038/s41598-021-03448-9
Publication status	Published - 2021 Dec

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abstract = "Construction of the hydroquinoline skeleton of symbioimine by Cu-mediated N-alkenylation or O-alkenylation of an allyl aminoalcohol, in which either chemoselectivity could lead to the target compound, was investigated. O-alkenylation followed by Claisen rearrangement was favored with high selectivity under a ligand-free condition. Subsequent intramolecular condensation furnished the hydroquinoline skeleton of symbioimine.",

author = "Rie Fujita and Kengo Hanaya and Takeshi Sugai and Shuhei Higashibayashi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Nos. JP20K05499 (S.H.) and JP21J14458 (R.F.), and funds from the Fukuoka Naohiko Memorial Foundation (S.H.). Publisher Copyright: {\textcopyright} 2021, The Author(s).",

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AU - Higashibayashi, Shuhei

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Nos. JP20K05499 (S.H.) and JP21J14458 (R.F.), and funds from the Fukuoka Naohiko Memorial Foundation (S.H.). Publisher Copyright: © 2021, The Author(s).

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Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine

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