Asymmetric Three-Component Heck Arylation/Amination of Nonconjugated Cyclodienes

Daoyong Zhu; Zhiwei Jiao; Yonggui Robin Chi; Théo P. Gonçalves; Kuo Wei Huang; Jianrong Steve Zhou

doi:10.1002/anie.201915864

Asymmetric Three-Component Heck Arylation/Amination of Nonconjugated Cyclodienes

Daoyong Zhu, Zhiwei Jiao, Yonggui Robin Chi, Théo P. Gonçalves, Kuo Wei Huang, Jianrong Steve Zhou^*

^*Corresponding author for this work

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

42 Citations (Scopus)

Abstract

Substituted cyclohexylamines are becoming increasingly important in drug discovery. Asymmetric Heck insertion/amination of nonconjugated cyclodienes proceeds to give 5-aryl cyclohexenylamines with good enantioselectivity and exclusive trans configurations. Primary and secondary anilines, indoline, and benzylamines are suitable amines. The weakly donating diphosphite Kelliphite forms a deep unsymmetrical pocket, which is essential for stereoselective anti attack of amines.

Original language	English
Pages (from-to)	5341-5345
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	13
DOIs	https://doi.org/10.1002/anie.201915864
Publication status	Published - Mar 23 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

allylic amination
Heck reaction
metal migration
palladium
phosphites

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10.1002/anie.201915864

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abstract = "Substituted cyclohexylamines are becoming increasingly important in drug discovery. Asymmetric Heck insertion/amination of nonconjugated cyclodienes proceeds to give 5-aryl cyclohexenylamines with good enantioselectivity and exclusive trans configurations. Primary and secondary anilines, indoline, and benzylamines are suitable amines. The weakly donating diphosphite Kelliphite forms a deep unsymmetrical pocket, which is essential for stereoselective anti attack of amines.",

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AU - Zhu, Daoyong

AU - Jiao, Zhiwei

AU - Chi, Yonggui Robin

AU - Gonçalves, Théo P.

AU - Huang, Kuo Wei

AU - Zhou, Jianrong Steve

PY - 2020/3/23

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N2 - Substituted cyclohexylamines are becoming increasingly important in drug discovery. Asymmetric Heck insertion/amination of nonconjugated cyclodienes proceeds to give 5-aryl cyclohexenylamines with good enantioselectivity and exclusive trans configurations. Primary and secondary anilines, indoline, and benzylamines are suitable amines. The weakly donating diphosphite Kelliphite forms a deep unsymmetrical pocket, which is essential for stereoselective anti attack of amines.

AB - Substituted cyclohexylamines are becoming increasingly important in drug discovery. Asymmetric Heck insertion/amination of nonconjugated cyclodienes proceeds to give 5-aryl cyclohexenylamines with good enantioselectivity and exclusive trans configurations. Primary and secondary anilines, indoline, and benzylamines are suitable amines. The weakly donating diphosphite Kelliphite forms a deep unsymmetrical pocket, which is essential for stereoselective anti attack of amines.

KW - allylic amination

KW - Heck reaction

KW - metal migration

KW - palladium

KW - phosphites

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Asymmetric Three-Component Heck Arylation/Amination of Nonconjugated Cyclodienes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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