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A novel organocatalyst for direct asymmetric Michael additions of cyclohexanone to nitroolefins

Paper ID Volume ID Publish Year Pages File Format Full-Text
50333 46790 2013 5 PDF Available
Title
A novel organocatalyst for direct asymmetric Michael additions of cyclohexanone to nitroolefins
Abstract

A novel catalyst combining pyrrolidinyl and cyclohexanediamine was designed and synthesized. Only 5 mol% of catalyst loading was required for enantioselective Michael additions of cyclohexanone and nitroolefins affording desired γ-nitroketones with > 99% yield, up to 91% ee and up to > 99/1 dr under mild conditions. The enantioselectivity of the product could be further improved to > 99% ee after a single recrystallization in petroleum ether/ethyl acetate.

Graphical abstractA novel catalyst composed of a chiral pyrrolidinyl and a chiral cyclohexanediamine framework was synthesized and employed as an efficient organocatalyst, and successfully applied in the asymmetric Michael additions of cyclohexanone to nitroolefins affording desired γ-nitroketones with good yields, and good stereoselectivities with a low catalyst loading at room temperature.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A novel organocatalyst was designed and synthesized. ► The catalyst contained a chiral pyrrolidinyl and cyclohexanediamine framework. ► It was used in asymmetric Michael reactions between cyclohexanone and nitroolefins. ► The reactions afforded γ-nitroketones with good yields and stereoselectivities. ► The process was performed under mild conditions with low catalyst loading.

Keywords
Organocatalyst; Asymmetric Michael reaction; Chiral cyclohexanediamine derivatives
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A novel organocatalyst for direct asymmetric Michael additions of cyclohexanone to nitroolefins
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 32, 5 February 2013, Pages 18–22
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
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Price was $35.95
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