Enantioselective Three-Component Coupling of Heteroarenes, Cycloalkenes and Propargylic Acetates

Shenghan Teng; Yonggui Robin Chi; Jianrong Steve Zhou

doi:10.1002/anie.202014781

Enantioselective Three-Component Coupling of Heteroarenes, Cycloalkenes and Propargylic Acetates

Shenghan Teng, Yonggui Robin Chi, Jianrong Steve Zhou^*

^*Corresponding author for this work

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

35 Citations (Scopus)

Abstract

Asymmetric coupling proceeds efficiently between propargylic acetates, cycloalkenes and electron-rich heteroarenes including indoles, pyrroles, activated furans and thiophenes. 2,3-Disubstituted tetrahydrofurans and pyrrolidines are produced in trans configuration and excellent enantiomeric ratios. The reaction proceeds via Wacker-type attack of nucleophilic heteroarenes on alkenes activated by allenyl Pd^II species.

Original language	English
Pages (from-to)	4491-4495
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	9
DOIs	https://doi.org/10.1002/anie.202014781
Publication status	Published - Feb 23 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH GmbH

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

alkene difunctionalization
allenes
heteroarylation
palladium catalysis
Wacker reaction

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10.1002/anie.202014781

Cite this

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abstract = "Asymmetric coupling proceeds efficiently between propargylic acetates, cycloalkenes and electron-rich heteroarenes including indoles, pyrroles, activated furans and thiophenes. 2,3-Disubstituted tetrahydrofurans and pyrrolidines are produced in trans configuration and excellent enantiomeric ratios. The reaction proceeds via Wacker-type attack of nucleophilic heteroarenes on alkenes activated by allenyl PdII species.",

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AU - Teng, Shenghan

AU - Chi, Yonggui Robin

AU - Zhou, Jianrong Steve

PY - 2021/2/23

Y1 - 2021/2/23

N2 - Asymmetric coupling proceeds efficiently between propargylic acetates, cycloalkenes and electron-rich heteroarenes including indoles, pyrroles, activated furans and thiophenes. 2,3-Disubstituted tetrahydrofurans and pyrrolidines are produced in trans configuration and excellent enantiomeric ratios. The reaction proceeds via Wacker-type attack of nucleophilic heteroarenes on alkenes activated by allenyl PdII species.

AB - Asymmetric coupling proceeds efficiently between propargylic acetates, cycloalkenes and electron-rich heteroarenes including indoles, pyrroles, activated furans and thiophenes. 2,3-Disubstituted tetrahydrofurans and pyrrolidines are produced in trans configuration and excellent enantiomeric ratios. The reaction proceeds via Wacker-type attack of nucleophilic heteroarenes on alkenes activated by allenyl PdII species.

KW - alkene difunctionalization

KW - allenes

KW - heteroarylation

KW - palladium catalysis

KW - Wacker reaction

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 9

ER -

Enantioselective Three-Component Coupling of Heteroarenes, Cycloalkenes and Propargylic Acetates

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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