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

^*Corresponding author for this work

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

58 Citations (Scopus)

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
Publication status	Published - Sept 18 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.5b02066

Cite this

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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",

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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

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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.

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