Highly enantioselective [3+3] cycloaddition of aromatic azomethine imines with cyclopropanes directed by π-π Stacking interactions

You Yun Zhou; Jun Li; Lin Ling; Sai Hu Liao; Xiu Li Sun; Yu Xue Li; Li Jia Wang; Yong Tang

doi:10.1002/anie.201207576

Highly enantioselective [3+3] cycloaddition of aromatic azomethine imines with cyclopropanes directed by π-π Stacking interactions

You Yun Zhou
, Jun Li
, Lin Ling
, Sai Hu Liao
, Xiu Li Sun^*
, Yu Xue Li
, Li Jia Wang
, Yong Tang

^*Corresponding author for this work

CAS - Shanghai Institute of Organic Chemistry

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

174 Scopus citations

Abstract

Designing armory: The side-arm-modified In-TOX/Ni^II complex was identified as a highly efficient and stereoselective catalyst for the [3+3] cycloaddition of aromatic azomethine imines with cyclopropanes (see picture). Density functional calculations and control experiments revealed that the directing effect of the side arm through π interactions is crucial to the stereochemical control.

Original language	English
Pages (from-to)	1452-1456
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	5
DOIs	https://doi.org/10.1002/anie.201207576
State	Published - 28 Jan 2013
Externally published	Yes

Keywords

[3+3] cycloaddition
dihydroisoquinolines
nickel
π interactions

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10.1002/anie.201207576

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title = "Highly enantioselective [3+3] cycloaddition of aromatic azomethine imines with cyclopropanes directed by π-π Stacking interactions",

abstract = "Designing armory: The side-arm-modified In-TOX/NiII complex was identified as a highly efficient and stereoselective catalyst for the [3+3] cycloaddition of aromatic azomethine imines with cyclopropanes (see picture). Density functional calculations and control experiments revealed that the directing effect of the side arm through π interactions is crucial to the stereochemical control.",

keywords = "[3+3] cycloaddition, dihydroisoquinolines, nickel, π interactions",

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T1 - Highly enantioselective [3+3] cycloaddition of aromatic azomethine imines with cyclopropanes directed by π-π Stacking interactions

AU - Zhou, You Yun

AU - Li, Jun

AU - Ling, Lin

AU - Liao, Sai Hu

AU - Sun, Xiu Li

AU - Li, Yu Xue

AU - Wang, Li Jia

AU - Tang, Yong

PY - 2013/1/28

Y1 - 2013/1/28

N2 - Designing armory: The side-arm-modified In-TOX/NiII complex was identified as a highly efficient and stereoselective catalyst for the [3+3] cycloaddition of aromatic azomethine imines with cyclopropanes (see picture). Density functional calculations and control experiments revealed that the directing effect of the side arm through π interactions is crucial to the stereochemical control.

AB - Designing armory: The side-arm-modified In-TOX/NiII complex was identified as a highly efficient and stereoselective catalyst for the [3+3] cycloaddition of aromatic azomethine imines with cyclopropanes (see picture). Density functional calculations and control experiments revealed that the directing effect of the side arm through π interactions is crucial to the stereochemical control.

KW - [3+3] cycloaddition

KW - dihydroisoquinolines

KW - nickel

KW - π interactions

UR - https://www.scopus.com/pages/publications/84872837213

U2 - 10.1002/anie.201207576

DO - 10.1002/anie.201207576

M3 - 文章

AN - SCOPUS:84872837213

SN - 1433-7851

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SP - 1452

EP - 1456

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 5

ER -

Highly enantioselective [3+3] cycloaddition of aromatic azomethine imines with cyclopropanes directed by π-π Stacking interactions

Abstract

Keywords

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