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DOI: 10.1055/s-2002-33506
Metal-Assisted Stereocontrol of 1,3-Dipolar Cycloaddition Reactions
Publication History
Publication Date:
17 September 2002 (online)
Abstract
A study on the metal ion-mediated stereo- and regiocontrol of 1,3-dipolar cycloaddition reactions, which have been developed and established in Kyushu University in Kasuga, is reviewed in this account. The first success involves the generation of metal-containing 1,3-dipoles. N-Metalated azomethine ylides are generated under reversible and irreversible conditions and undergo exclusively endo-selective 1,3-dipolar cycloadditions with carbonyl-activated alkenes through the chelated transition structure. The closely related intermediates derived from bulky imine esters can be utilized for the anti-selective Michael additions. The second topic is the regio- and syn-selective nitrone and nitrile oxide cycloadditions to allylic alcohols in the presence of magnesium ions. These reactions are magnesium ion specific. Lewis acid-mediated nitrone cycloadditions to electron-deficient alkenes have been also been discovered in Kasuga and this discovery was a starting point for the chiral Lewis acid catalyzed enantioselective nitrone cycloadditions. With powerful Lewis acid catalysts in hand, the author’s group has developed highly efficient enantioselective nitrone cycloadditions and diazo cycloadditions catalyzed by the transition metal aqua complexes derived from the DBFOX/Ph ligand.
Key words
1,3-dipolar cycloaddition - Lewis acid catalyst - regio- and stereocontrol - enantiocontrol - N-metalated azomethine ylide - nitrone - nitrile oxide - diazo alkane - magnesium ions - allylic alcohol - enantioselective nitrone cycloaddition - enantioselective diazo cycloaddition
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1a
1,3-Dipolar
Cycloaddition Chemistry
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1b
1,3-Dipolar Cycloaddition
Chemistry
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References
Kanemasa, S.; Shirahase, M. unpublished result.