Asymmetric Diels–Alder reaction between furans and propiolates

Akihiro Ogura; Taisuke Ito; Koujiro Moriya; Hiroki Horigome; Ken ichi Takao

doi:10.1016/j.tetlet.2021.153075

Asymmetric Diels–Alder reaction between furans and propiolates

Akihiro Ogura, Taisuke Ito, Koujiro Moriya, Hiroki Horigome, Ken ichi Takao

応用化学科

研究成果: Article › 査読

1 被引用数 (Scopus)

抄録

We report the first asymmetric Diels–Alder reaction between furan and propiolates. Propiolate, a dienophile, was equipped with an Evans’ auxiliary and a sulfonyl group to control and facilitate diastereoselective cycloaddition. Treatment with furan as a diene and aluminium Lewis acid afforded a 7-oxabicyclo[2.2.1]heptadiene skeleton diastereoselectively. The origin of diastereoselectivity can be explained by chelation of aluminium center to carbonyl groups and oxygen of furan. Friedel–Crafts-type products were obtained when pyrrole was used as diene.

本文言語	English
論文番号	153075
ジャーナル	Tetrahedron Letters
巻	72
DOI	https://doi.org/10.1016/j.tetlet.2021.153075
出版ステータス	Published - 2021 5月 25

ASJC Scopus subject areas

生化学
創薬
有機化学

文献へのアクセス

10.1016/j.tetlet.2021.153075

他のファイルとリンク

引用スタイル

@article{08b9f00a9ddd42cabd811d44251f37b6,

title = "Asymmetric Diels–Alder reaction between furans and propiolates",

abstract = "We report the first asymmetric Diels–Alder reaction between furan and propiolates. Propiolate, a dienophile, was equipped with an Evans{\textquoteright} auxiliary and a sulfonyl group to control and facilitate diastereoselective cycloaddition. Treatment with furan as a diene and aluminium Lewis acid afforded a 7-oxabicyclo[2.2.1]heptadiene skeleton diastereoselectively. The origin of diastereoselectivity can be explained by chelation of aluminium center to carbonyl groups and oxygen of furan. Friedel–Crafts-type products were obtained when pyrrole was used as diene.",

keywords = "Diels–Alder reaction, Furan, Propiolate",

author = "Akihiro Ogura and Taisuke Ito and Koujiro Moriya and Hiroki Horigome and Takao, {Ken ichi}",

note = "Funding Information: This research was supported by JSPS KAKENHI Grant Number 19 K15571, the Tobe Maki Scholarship Foundation, Keio Gijuku Academic Development Funds, and Keio Leading-edge Laboratory of Science and Technology for financial support. Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

year = "2021",

month = may,

day = "25",

doi = "10.1016/j.tetlet.2021.153075",

language = "English",

volume = "72",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

}

TY - JOUR

T1 - Asymmetric Diels–Alder reaction between furans and propiolates

AU - Ogura, Akihiro

AU - Ito, Taisuke

AU - Moriya, Koujiro

AU - Horigome, Hiroki

AU - Takao, Ken ichi

N1 - Funding Information: This research was supported by JSPS KAKENHI Grant Number 19 K15571, the Tobe Maki Scholarship Foundation, Keio Gijuku Academic Development Funds, and Keio Leading-edge Laboratory of Science and Technology for financial support. Publisher Copyright: © 2021 Elsevier Ltd

PY - 2021/5/25

Y1 - 2021/5/25

N2 - We report the first asymmetric Diels–Alder reaction between furan and propiolates. Propiolate, a dienophile, was equipped with an Evans’ auxiliary and a sulfonyl group to control and facilitate diastereoselective cycloaddition. Treatment with furan as a diene and aluminium Lewis acid afforded a 7-oxabicyclo[2.2.1]heptadiene skeleton diastereoselectively. The origin of diastereoselectivity can be explained by chelation of aluminium center to carbonyl groups and oxygen of furan. Friedel–Crafts-type products were obtained when pyrrole was used as diene.

AB - We report the first asymmetric Diels–Alder reaction between furan and propiolates. Propiolate, a dienophile, was equipped with an Evans’ auxiliary and a sulfonyl group to control and facilitate diastereoselective cycloaddition. Treatment with furan as a diene and aluminium Lewis acid afforded a 7-oxabicyclo[2.2.1]heptadiene skeleton diastereoselectively. The origin of diastereoselectivity can be explained by chelation of aluminium center to carbonyl groups and oxygen of furan. Friedel–Crafts-type products were obtained when pyrrole was used as diene.

KW - Diels–Alder reaction

KW - Furan

KW - Propiolate

UR - http://www.scopus.com/inward/record.url?scp=85106241830&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85106241830&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2021.153075

DO - 10.1016/j.tetlet.2021.153075

M3 - Article

AN - SCOPUS:85106241830

VL - 72

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

M1 - 153075

ER -

Asymmetric Diels–Alder reaction between furans and propiolates

抄録

ASJC Scopus subject areas

文献へのアクセス

他のファイルとリンク

フィンガープリント

引用スタイル