De novo approach to izidines via a gold-catalyzed hydroamination-n-acyliminium ion cyclization of acyclic ynamides

Kenji Sugimoto; Shota Mizuno; Misaki Shirato; Kosuke Tanabe; Yuji Matsuya

doi:10.3987/COM-20-S(K)38

De novo approach to izidines via a gold-catalyzed hydroamination-n-acyliminium ion cyclization of acyclic ynamides

Kenji Sugimoto^*, Shota Mizuno, Misaki Shirato, Kosuke Tanabe, Yuji Matsuya^*

^*Corresponding author for this work

Synthetic and Medicinal Chemistry

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

1 Scopus citations

Abstract

A gold(I)-catalyzed novel domino reaction of acyclic ynamides yielding nitrogen-fused bicyclic skeletons was described. The reaction with 10 mol% JohnPhosAuNTf₂ and stoichiometric amount of PhCO₂H enables constructions of quinolizidine and indolizidine skeleton having tetrasubstituted carbon center. Especially in the case of quinolizidine synthesis, the quaternary stereogenic center could be furnished under highly diastereoselective manner.

Original language	English
Journal	Heterocycles
Volume	103
Issue number	1
DOIs	https://doi.org/10.3987/COM-20-S(K)38
State	Published - 2021

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "De novo approach to izidines via a gold-catalyzed hydroamination-n-acyliminium ion cyclization of acyclic ynamides",

abstract = "A gold(I)-catalyzed novel domino reaction of acyclic ynamides yielding nitrogen-fused bicyclic skeletons was described. The reaction with 10 mol% JohnPhosAuNTf2 and stoichiometric amount of PhCO2H enables constructions of quinolizidine and indolizidine skeleton having tetrasubstituted carbon center. Especially in the case of quinolizidine synthesis, the quaternary stereogenic center could be furnished under highly diastereoselective manner.",

author = "Kenji Sugimoto and Shota Mizuno and Misaki Shirato and Kosuke Tanabe and Yuji Matsuya",

year = "2021",

doi = "10.3987/COM-20-S(K)38",

language = "英語",

volume = "103",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "1",

}

TY - JOUR

T1 - De novo approach to izidines via a gold-catalyzed hydroamination-n-acyliminium ion cyclization of acyclic ynamides

AU - Sugimoto, Kenji

AU - Mizuno, Shota

AU - Shirato, Misaki

AU - Tanabe, Kosuke

AU - Matsuya, Yuji

PY - 2021

Y1 - 2021

N2 - A gold(I)-catalyzed novel domino reaction of acyclic ynamides yielding nitrogen-fused bicyclic skeletons was described. The reaction with 10 mol% JohnPhosAuNTf2 and stoichiometric amount of PhCO2H enables constructions of quinolizidine and indolizidine skeleton having tetrasubstituted carbon center. Especially in the case of quinolizidine synthesis, the quaternary stereogenic center could be furnished under highly diastereoselective manner.

AB - A gold(I)-catalyzed novel domino reaction of acyclic ynamides yielding nitrogen-fused bicyclic skeletons was described. The reaction with 10 mol% JohnPhosAuNTf2 and stoichiometric amount of PhCO2H enables constructions of quinolizidine and indolizidine skeleton having tetrasubstituted carbon center. Especially in the case of quinolizidine synthesis, the quaternary stereogenic center could be furnished under highly diastereoselective manner.

UR - http://www.scopus.com/inward/record.url?scp=85108248927&partnerID=8YFLogxK

U2 - 10.3987/COM-20-S(K)38

DO - 10.3987/COM-20-S(K)38

M3 - 学術論文

AN - SCOPUS:85108248927

SN - 0385-5414

VL - 103

JO - Heterocycles

JF - Heterocycles

IS - 1

ER -

De novo approach to izidines via a gold-catalyzed hydroamination-n-acyliminium ion cyclization of acyclic ynamides

Abstract

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