B(C6F5)3: A New Class of Strong and Bulky Lewis Acid for Exo-Selective Intermolecular Diels-Alder Reactions of Unreactive Acyclic Dienes with α,β-Enals

Jia Hui Zhou; Bing Jiang; Fei Fan Meng; Yun He Xu; Teck Peng Loh

doi:10.1021/acs.orglett.5b02066

B(C₆F₅)₃: A New Class of Strong and Bulky Lewis Acid for Exo-Selective Intermolecular Diels-Alder Reactions of Unreactive Acyclic Dienes with α,β-Enals

Jia Hui Zhou, Bing Jiang, Fei Fan Meng, Yun He Xu, Teck Peng Loh

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

56 Scopus citations

Abstract

Lewis acid B(C₆F₅)₃ catalyzed the Diels-Alder reactions of multisubstituted open-chain dienes and α,β-enals to afford the desired products with high exo-selectivities are reported. The substituent effect of the dienes and dienophiles on the products stereoselectivity was thoroughly investigated, and it was found that most of the desired exo-Diels-Alder products could be obtained in good yields and with high exo-stereoselectivities.

Original language	English
Pages (from-to)	4432-4435
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.5b02066
State	Published - 18 Sep 2015
Externally published	Yes

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title = "B(C6F5)3: A New Class of Strong and Bulky Lewis Acid for Exo-Selective Intermolecular Diels-Alder Reactions of Unreactive Acyclic Dienes with α,β-Enals",

abstract = "Lewis acid B(C6F5)3 catalyzed the Diels-Alder reactions of multisubstituted open-chain dienes and α,β-enals to afford the desired products with high exo-selectivities are reported. The substituent effect of the dienes and dienophiles on the products stereoselectivity was thoroughly investigated, and it was found that most of the desired exo-Diels-Alder products could be obtained in good yields and with high exo-stereoselectivities.",

author = "Zhou, {Jia Hui} and Bing Jiang and Meng, {Fei Fan} and Xu, {Yun He} and Loh, {Teck Peng}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = sep,

day = "18",

doi = "10.1021/acs.orglett.5b02066",

language = "英语",

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T1 - B(C6F5)3

T2 - A New Class of Strong and Bulky Lewis Acid for Exo-Selective Intermolecular Diels-Alder Reactions of Unreactive Acyclic Dienes with α,β-Enals

AU - Zhou, Jia Hui

AU - Jiang, Bing

AU - Meng, Fei Fan

AU - Xu, Yun He

AU - Loh, Teck Peng

PY - 2015/9/18

Y1 - 2015/9/18

N2 - Lewis acid B(C6F5)3 catalyzed the Diels-Alder reactions of multisubstituted open-chain dienes and α,β-enals to afford the desired products with high exo-selectivities are reported. The substituent effect of the dienes and dienophiles on the products stereoselectivity was thoroughly investigated, and it was found that most of the desired exo-Diels-Alder products could be obtained in good yields and with high exo-stereoselectivities.

AB - Lewis acid B(C6F5)3 catalyzed the Diels-Alder reactions of multisubstituted open-chain dienes and α,β-enals to afford the desired products with high exo-selectivities are reported. The substituent effect of the dienes and dienophiles on the products stereoselectivity was thoroughly investigated, and it was found that most of the desired exo-Diels-Alder products could be obtained in good yields and with high exo-stereoselectivities.

UR - http://www.scopus.com/inward/record.url?scp=84941904818&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b02066

DO - 10.1021/acs.orglett.5b02066

M3 - 文章

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SN - 1523-7060

VL - 17

SP - 4432

EP - 4435

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

B(C₆F₅)₃: A New Class of Strong and Bulky Lewis Acid for Exo-Selective Intermolecular Diels-Alder Reactions of Unreactive Acyclic Dienes with α,β-Enals

Abstract

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