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Enantioselective cyanation of aldehydes catalyzed by bifunctional salen–aluminum complex

Paper ID Volume ID Publish Year Pages File Format Full-Text
49986 46775 2012 3 PDF Available
Title
Enantioselective cyanation of aldehydes catalyzed by bifunctional salen–aluminum complex
Abstract

Chiral N-oxide salen ligands and their corresponding Al complexes were synthesized. Notably, the catalytic activity and asymmetric induction ability of the bifunctional N-oxide salen-Al for asymmetric cyanosilylation were compared with that of bi-component catalyst system including chiral pyrrolidine salen–Al complex and Ph3PO. Interestingly, introducing N-oxide group in salen unit could enhance the activity and enantioselectivity of bifunctional catalyst without further adding Ph3PO as co-catalyst and inverse configurations were generated from the two systems. In addition, excellent yields and high ee values could be obtained under milder conditions in bifunctional catalyst system compared with that of bi-component catalyst system.

Graphical abstractBoth bifunctional N-oxide salen-Al(III) and bi-component complexes including pyrrolidine salen-Al(III)/Ph3PO exhibited highly efficient and enantioselective activities for the asymmetric addition of trimethylsilyl cyanide to aldehydes. And inverse configurations were generated from the two systems.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Bifunctional salen–aluminium complexes were synthesized. ► Its catalytic activity and asymmetric induction ability were investigated. ► Excellent yields and high ee values could be obtained under milder conditions. ► Inverse configuration was obtained from bifunctional or bicomponent system.

Keywords
Asymmetric cyanosilylation; Bifunctional catalyst; Bi-component catalyst; Salen–Al complex
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Enantioselective cyanation of aldehydes catalyzed by bifunctional salen–aluminum complex
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 27, 5 October 2012, Pages 138–140
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Price was $35.95
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Price after discount Only $4.95
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Full-text PDF Download
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