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

Department of Applied Chemistry

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

3 Citations (Scopus)

Abstract

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.

Original language	English
Article number	153075
Journal	Tetrahedron Letters
Volume	72
DOIs	https://doi.org/10.1016/j.tetlet.2021.153075
Publication status	Published - 2021 May 25

Keywords

Diels–Alder reaction
Furan
Propiolate

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2021.153075

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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",

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

language = "English",

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journal = "Tetrahedron Letters",

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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

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DO - 10.1016/j.tetlet.2021.153075

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SN - 0040-4039

VL - 72

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153075

ER -

Asymmetric Diels–Alder reaction between furans and propiolates

Abstract

Keywords

ASJC Scopus subject areas

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