Diene-Transmissive Enantioselective Diels-Alder Reactions and Sequences Involving Substituted Dendralenes
dc.contributor.author | Sherburn, Michael | |
dc.contributor.author | George, Josemon | |
dc.date.accessioned | 2020-09-22T01:16:18Z | |
dc.date.issued | 2019 | |
dc.date.updated | 2020-06-23T00:57:15Z | |
dc.description.abstract | Readily 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]dendralene | en_AU |
dc.description.sponsorship | This work was supported by the Australian Research Council (DP160104322). | en_AU |
dc.format.mimetype | application/pdf | en_AU |
dc.identifier.issn | 0022-3263 | en_AU |
dc.identifier.uri | http://hdl.handle.net/1885/211324 | |
dc.language.iso | en_AU | en_AU |
dc.publisher | American Chemical Society | en_AU |
dc.relation | http://purl.org/au-research/grants/arc/DP160104322 | en_AU |
dc.rights | © 2019 American Chemical Society | en_AU |
dc.source | Journal of Organic Chemistry | en_AU |
dc.title | Diene-Transmissive Enantioselective Diels-Alder Reactions and Sequences Involving Substituted Dendralenes | en_AU |
dc.type | Journal article | en_AU |
local.bibliographicCitation.issue | 22 | en_AU |
local.bibliographicCitation.lastpage | 14723 | en_AU |
local.bibliographicCitation.startpage | 14712 | en_AU |
local.contributor.affiliation | Sherburn, Michael, College of Science, ANU | en_AU |
local.contributor.affiliation | George, Josemon, College of Science, ANU | en_AU |
local.contributor.authoremail | u4053118@anu.edu.au | en_AU |
local.contributor.authoruid | Sherburn, Michael, u4053118 | en_AU |
local.contributor.authoruid | George, Josemon, u5465582 | en_AU |
local.description.embargo | 2037-12-31 | |
local.description.notes | Imported from ARIES | en_AU |
local.identifier.absfor | 030503 - Organic Chemical Synthesis | en_AU |
local.identifier.absseo | 970104 - Expanding Knowledge in the Earth Sciences | en_AU |
local.identifier.ariespublication | u5786633xPUB1437 | en_AU |
local.identifier.citationvolume | 84 | en_AU |
local.identifier.doi | 10.1021/acs.joc.9b02296 | en_AU |
local.identifier.thomsonID | WOS:000497259900033 | |
local.identifier.uidSubmittedBy | u5786633 | en_AU |
local.publisher.url | http://pubs.acs.org/journal/joceah/about.html | en_AU |
local.type.status | Published Version | en_AU |
Downloads
Original bundle
1 - 1 of 1
No Thumbnail Available
- Name:
- 01_Sherburn_Diene-Transmissive_2019.pdf
- Size:
- 1.26 MB
- Format:
- Adobe Portable Document Format