About: Mechanistic Studies of Hydrazide-CatalyzedEnantioselective Diels−Alder Reactions

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Attributs	Valeurs
type	work Article
Is Part Of	http://hub.abes.fr/acs/periodical/joceah/2006/volume_71/issue_12/w
Subject	Note
Title	Mechanistic Studies of Hydrazide-CatalyzedEnantioselective Diels−Alder Reactions
has manifestation of work	http://hub.abes.fr/acs/periodical/joceah/2006/volume_71/issue_12/101021jo060339p/m/web http://hub.abes.fr/acs/periodical/joceah/2006/volume_71/issue_12/101021jo060339p/m/print
related by	http://hub.abes.fr/acs/periodical/joceah/2006/volume_71/issue_12/101021jo060339p/authorship/2 http://hub.abes.fr/acs/periodical/joceah/2006/volume_71/issue_12/101021jo060339p/authorship/1
Author	Lemay Mathieu Ogilvie William W.
Abstract	The mechanism of the enantioselective, hydrazide-catalyzedDiels−Alder cycloaddition was investigated in detail. Boththe formation of the reactive iminium species and thehydrolysis of the product iminium intermediates were foundto be extremely rapid, leaving the cycloaddition as thekinetically significant step. Mechanistic studies using NMRshowed that a retro-Diels−Alder reaction occurred duringthe catalytic cycle, suggesting a thermodynamic componentto the reaction.
article type	brief-report
is part of this journal	The Journal of Organic Chemistry

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