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Asymmetric 1,4-disubstitution of 1,3-dienes: Palladium(II)-catalyzed formation of azido-ketones from 1,3-cyclohexadiene

Paper ID Volume ID Publish Year Pages File Format Full-Text
51921 46858 2008 5 PDF Available
Title
Asymmetric 1,4-disubstitution of 1,3-dienes: Palladium(II)-catalyzed formation of azido-ketones from 1,3-cyclohexadiene
Abstract

The oxidation of cyclohexadiene in a mixed aqueous solvent in the present of azide ion produced 4-azido-2-cyclohexene-1-one, 1, and 2-azido-3-cyclohexene-1-one, 2, in a four electron transfer in about a 70% yield. The overall reaction is a net air oxidation. These enantioselectivies are higher than any obtained previously for addition to 1,3-dienes. The conversion of 1 to 2 involves a [3,3]sigmatropic rearrangement.

Keywords
Palladium(II); Cyclohexadiene; Oxidation; Azide; Ketone; Asymmetric
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Asymmetric 1,4-disubstitution of 1,3-dienes: Palladium(II)-catalyzed formation of azido-ketones from 1,3-cyclohexadiene
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 9, Issue 7, 1 April 2008, Pages 1661–1665
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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