Enantioselective oxazaborolidinium-catalyzed Diels - Alder reactions without CH....O hydrogen bonding

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dc.contributor.authorPaddon-Row, Michaelen_AU
dc.contributor.authorKwan, Laurenceen_AU
dc.contributor.authorWillis, Anthonyen_AU
dc.contributor.authorSherburn, Michaelen_AU
dc.date.accessioned2015-12-10T22:21:01Z
dc.date.issued2008
dc.date.updated2016-02-24T10:22:48Z
dc.description.abstract(Chemical Equation Presented) All cis-tems go! The first detailed computational investigations into the title reaction validate Corey's two pre-transition-state models and reveal a third Lewis acid coordination mode (see picture), which operates for esters having s-cis C=C-C=O groups. The new pre-transition-state model explains the unexpected enantioselectivity witnessed for several Diels-Alder reactions and does not involve a C-H⋯O hydrogen bond.
dc.identifier.issn1433-7851
dc.identifier.urihttp://hdl.handle.net/1885/52195
dc.publisherWiley-VCH Verlag GMBH
dc.sourceAngewandte Chemie International Edition
dc.subjectKeywords: Asymmetric catalysis; Density functional calculations; Lewis acids; Lewis bases; Transition states
dc.titleEnantioselective oxazaborolidinium-catalyzed Diels - Alder reactions without CH....O hydrogen bonding
dc.typeJournal article
local.bibliographicCitation.issue37
local.bibliographicCitation.lastpage7017
local.bibliographicCitation.startpage7013
local.contributor.affiliationPaddon-Row, Michael, University of New South Wales
local.contributor.affiliationKwan, Laurence, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationSherburn, Michael, College of Physical and Mathematical Sciences, ANU
local.contributor.authoremailu8512028@anu.edu.au
local.contributor.authoruidKwan, Laurence, u4015006
local.contributor.authoruidWillis, Anthony, u8512028
local.contributor.authoruidSherburn, Michael, u4053118
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030799 - Theoretical and Computational Chemistry not elsewhere classified
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4005981xPUB241
local.identifier.citationvolume47
local.identifier.doi10.1002/anie.200802002
local.identifier.scopusID2-s2.0-54749116266
local.identifier.thomsonID000259041000010
local.identifier.uidSubmittedByu4005981
local.type.statusPublished Version

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