Diene-Transmissive Enantioselective Diels-Alder Reactions and Sequences Involving Substituted Dendralenes

dc.contributor.authorSherburn, Michael
dc.contributor.authorGeorge, Josemon
dc.date.accessioned2020-09-22T01:16:18Z
dc.date.issued2019
dc.date.updated2020-06-23T00:57:15Z
dc.description.abstractReadily available and stable substituted [3]- dendralenes undergo highly chemo-, regio-, diastereo-, and enantioselective organocatalyzed Diels−Alder reactions with acrolein to form enantiomerically enriched cycloadducts. These monocycloadducts carry semicyclic dienes that undergo a second, substrate-controlled diastereoselective Diels−Alder reaction with a different dienophile to form 2-fold cycloadducts. Overall, annulated, functional group rich, chiral Δ1(9)- octalin building blocks are accessed in one-pot operations that significantly extend the preparative value of diene-transmissive Diels−Alder sequences since they offer products of regio- and stereochemistry complementary to those generated from the parent, unsubstituted [3]dendraleneen_AU
dc.description.sponsorshipThis work was supported by the Australian Research Council (DP160104322).en_AU
dc.format.mimetypeapplication/pdfen_AU
dc.identifier.issn0022-3263en_AU
dc.identifier.urihttp://hdl.handle.net/1885/211324
dc.language.isoen_AUen_AU
dc.publisherAmerican Chemical Societyen_AU
dc.relationhttp://purl.org/au-research/grants/arc/DP160104322en_AU
dc.rights© 2019 American Chemical Societyen_AU
dc.sourceJournal of Organic Chemistryen_AU
dc.titleDiene-Transmissive Enantioselective Diels-Alder Reactions and Sequences Involving Substituted Dendralenesen_AU
dc.typeJournal articleen_AU
local.bibliographicCitation.issue22en_AU
local.bibliographicCitation.lastpage14723en_AU
local.bibliographicCitation.startpage14712en_AU
local.contributor.affiliationSherburn, Michael, College of Science, ANUen_AU
local.contributor.affiliationGeorge, Josemon, College of Science, ANUen_AU
local.contributor.authoremailu4053118@anu.edu.auen_AU
local.contributor.authoruidSherburn, Michael, u4053118en_AU
local.contributor.authoruidGeorge, Josemon, u5465582en_AU
local.description.embargo2037-12-31
local.description.notesImported from ARIESen_AU
local.identifier.absfor030503 - Organic Chemical Synthesisen_AU
local.identifier.absseo970104 - Expanding Knowledge in the Earth Sciencesen_AU
local.identifier.ariespublicationu5786633xPUB1437en_AU
local.identifier.citationvolume84en_AU
local.identifier.doi10.1021/acs.joc.9b02296en_AU
local.identifier.thomsonIDWOS:000497259900033
local.identifier.uidSubmittedByu5786633en_AU
local.publisher.urlhttp://pubs.acs.org/journal/joceah/about.htmlen_AU
local.type.statusPublished Versionen_AU

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