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^*

^*この論文の責任著者

薬品製造学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

1 被引用数 (Scopus)

抄録

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.

本文言語	英語
ジャーナル	Heterocycles
巻	103
号	1
DOI	https://doi.org/10.3987/COM-20-S(K)38
出版ステータス	出版済み - 2021

ASJC Scopus 主題領域

分析化学
薬理学
有機化学

文献へのアクセス

10.3987/COM-20-S(K)38

引用スタイル

@article{ba4049e0fb024a0181d8101057c1ea30,

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

抄録

ASJC Scopus 主題領域

文献へのアクセス

フィンガープリント

引用スタイル