Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles

Xiaolei Huang; Minh Hieu Nguyen; Maoping Pu; Luoqiang Zhang; Yonggui Robin Chi; Yun Dong Wu; Jianrong Steve Zhou

doi:10.1002/anie.202000859

Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles

Xiaolei Huang, Minh Hieu Nguyen, Maoping Pu, Luoqiang Zhang, Yonggui Robin Chi, Yun Dong Wu, Jianrong Steve Zhou^*

^*Corresponding author for this work

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

24 Citations (Scopus)

Abstract

Conformationally restricted azabicycles are becoming increasingly important in medicinal research. Asymmetric Heck bicyclization of enynes proceeds to give medicinally useful aza[3.1.0] and aza[4.1.0] bicycles with excellent enantioselectivity. The key organopalladium species after bicyclization can be trapped by silanes and terminal alkynes.

Original language	English
Pages (from-to)	10814-10818
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	27
DOIs	https://doi.org/10.1002/anie.202000859
Publication status	Published - Jun 26 2020
Externally published	Yes

Bibliographical note

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

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

alkynylation
azabicycles
palladium
reductive Heck reaction
strained rings

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10.1002/anie.202000859

Cite this

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title = "Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles",

abstract = "Conformationally restricted azabicycles are becoming increasingly important in medicinal research. Asymmetric Heck bicyclization of enynes proceeds to give medicinally useful aza[3.1.0] and aza[4.1.0] bicycles with excellent enantioselectivity. The key organopalladium species after bicyclization can be trapped by silanes and terminal alkynes.",

keywords = "alkynylation, azabicycles, palladium, reductive Heck reaction, strained rings",

author = "Xiaolei Huang and Nguyen, {Minh Hieu} and Maoping Pu and Luoqiang Zhang and Chi, {Yonggui Robin} and Wu, {Yun Dong} and Zhou, {Jianrong Steve}",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2020",

month = jun,

day = "26",

doi = "10.1002/anie.202000859",

language = "English",

volume = "59",

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T1 - Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles

AU - Huang, Xiaolei

AU - Nguyen, Minh Hieu

AU - Pu, Maoping

AU - Zhang, Luoqiang

AU - Chi, Yonggui Robin

AU - Wu, Yun Dong

AU - Zhou, Jianrong Steve

PY - 2020/6/26

Y1 - 2020/6/26

N2 - Conformationally restricted azabicycles are becoming increasingly important in medicinal research. Asymmetric Heck bicyclization of enynes proceeds to give medicinally useful aza[3.1.0] and aza[4.1.0] bicycles with excellent enantioselectivity. The key organopalladium species after bicyclization can be trapped by silanes and terminal alkynes.

AB - Conformationally restricted azabicycles are becoming increasingly important in medicinal research. Asymmetric Heck bicyclization of enynes proceeds to give medicinally useful aza[3.1.0] and aza[4.1.0] bicycles with excellent enantioselectivity. The key organopalladium species after bicyclization can be trapped by silanes and terminal alkynes.

KW - alkynylation

KW - azabicycles

KW - palladium

KW - reductive Heck reaction

KW - strained rings

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DO - 10.1002/anie.202000859

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AN - SCOPUS:85085926507

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 27

ER -

Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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