Palladium/Lewis Acid Cocatalyzed Reductive Asymmetric Ring-Opening Reaction of Azabenzonorbornadienes with Tertiary Amines as the Hydrogen Source

Dapeng Zhang; Ruhima Khan; Fan Yang; Xuexin Zhang; Guoli Shen; Yang Gao; Ruifeng Fan; Weiqing Sun; Baomin Fan

doi:10.1002/ejoc.201800503

Palladium/Lewis Acid Cocatalyzed Reductive Asymmetric Ring-Opening Reaction of Azabenzonorbornadienes with Tertiary Amines as the Hydrogen Source

Dapeng Zhang
, Ruhima Khan^*
, Fan Yang
, Xuexin Zhang
, Guoli Shen
, Yang Gao
, Ruifeng Fan
, Weiqing Sun
, Baomin Fan

^*Corresponding author for this work

Yunnan Minzu University

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

10 Citations (Scopus)

Abstract

The reductive asymmetric ring-opening reaction of azabenzonorbornadienes has been developed by using palladium and silver as a co-catalytic system and various tertiary amines as the hydrogen source. A wide range of azabenzonorbornadienes that contain electron-donating and electron-withdrawing substituents performed well in the developed protocol to result in 1,2-dihydronaphthalen-1-amine derivatives in excellent yields with good to high enantioselectivities.

Original language	English
Pages (from-to)	3464-3470
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	26
DOIs	https://doi.org/10.1002/ejoc.201800503
Publication status	Published - 13 Jul 2018
Externally published	Yes

Keywords

Asymmetric synthesis
Enantioselectivity
Hydrogenation
Reduction
Ring-opening

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10.1002/ejoc.201800503

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title = "Palladium/Lewis Acid Cocatalyzed Reductive Asymmetric Ring-Opening Reaction of Azabenzonorbornadienes with Tertiary Amines as the Hydrogen Source",

abstract = "The reductive asymmetric ring-opening reaction of azabenzonorbornadienes has been developed by using palladium and silver as a co-catalytic system and various tertiary amines as the hydrogen source. A wide range of azabenzonorbornadienes that contain electron-donating and electron-withdrawing substituents performed well in the developed protocol to result in 1,2-dihydronaphthalen-1-amine derivatives in excellent yields with good to high enantioselectivities.",

keywords = "Asymmetric synthesis, Enantioselectivity, Hydrogenation, Reduction, Ring-opening",

author = "Dapeng Zhang and Ruhima Khan and Fan Yang and Xuexin Zhang and Guoli Shen and Yang Gao and Ruifeng Fan and Weiqing Sun and Baomin Fan",

note = "Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = jul,

day = "13",

doi = "10.1002/ejoc.201800503",

language = "English",

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journal = "European Journal of Organic Chemistry",

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T1 - Palladium/Lewis Acid Cocatalyzed Reductive Asymmetric Ring-Opening Reaction of Azabenzonorbornadienes with Tertiary Amines as the Hydrogen Source

AU - Zhang, Dapeng

AU - Khan, Ruhima

AU - Yang, Fan

AU - Zhang, Xuexin

AU - Shen, Guoli

AU - Gao, Yang

AU - Fan, Ruifeng

AU - Sun, Weiqing

AU - Fan, Baomin

PY - 2018/7/13

Y1 - 2018/7/13

N2 - The reductive asymmetric ring-opening reaction of azabenzonorbornadienes has been developed by using palladium and silver as a co-catalytic system and various tertiary amines as the hydrogen source. A wide range of azabenzonorbornadienes that contain electron-donating and electron-withdrawing substituents performed well in the developed protocol to result in 1,2-dihydronaphthalen-1-amine derivatives in excellent yields with good to high enantioselectivities.

AB - The reductive asymmetric ring-opening reaction of azabenzonorbornadienes has been developed by using palladium and silver as a co-catalytic system and various tertiary amines as the hydrogen source. A wide range of azabenzonorbornadienes that contain electron-donating and electron-withdrawing substituents performed well in the developed protocol to result in 1,2-dihydronaphthalen-1-amine derivatives in excellent yields with good to high enantioselectivities.

KW - Asymmetric synthesis

KW - Enantioselectivity

KW - Hydrogenation

KW - Reduction

KW - Ring-opening

UR - https://www.scopus.com/pages/publications/85050014183

U2 - 10.1002/ejoc.201800503

DO - 10.1002/ejoc.201800503

M3 - Article

AN - SCOPUS:85050014183

SN - 1434-193X

VL - 2018

SP - 3464

EP - 3470

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 26

ER -

Palladium/Lewis Acid Cocatalyzed Reductive Asymmetric Ring-Opening Reaction of Azabenzonorbornadienes with Tertiary Amines as the Hydrogen Source

Abstract

Keywords

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