Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes
| dc.contributor.author | Johnson, Kirsten | |
| dc.contributor.author | Schmidt, Adam | |
| dc.contributor.author | Stanley, Levi | |
| dc.contributor.department | Department of Chemistry | |
| dc.date | 2018-02-17T06:37:33.000 | |
| dc.date.accessioned | 2020-06-30T01:16:46Z | |
| dc.date.available | 2020-06-30T01:16:46Z | |
| dc.date.copyright | Thu Jan 01 00:00:00 UTC 2015 | |
| dc.date.issued | 2015-09-01 | |
| dc.description.abstract | <p>The development of a rhodium catalyst for <em>endo</em>- and enantioselective hydroacylation of<em>ortho</em>-allylbenzaldehydes is reported. A catalyst generated <em>in situ</em> from [Rh(COD)Cl]2, (<em>R</em>)-DTBM-SEGPHOS, and NaBARF promotes the desired hydroacylation reactions and minimizes the formation of byproducts from competitive alkene isomerization and ene/dehydration pathways. These rhodium-catalyzed processes generate the 3,4-dihydronaphthalen-1(2<em>H</em>)-one products in moderate-to-high yields (49–91%) with excellent enantioselectivities (96–99% ee).</p> | |
| dc.description.comments | <p>Reprinted (adapted) with permission from <em>Organic Letters</em> 17 (2015): 4654, doi:<a href="http://dx.doi.org/10.1021/acs.orglett.5b02559" target="_blank">10.1021/acs.orglett.5b02559</a>. Copyright 2015 American Chemical Society.</p> | |
| dc.format.mimetype | application/pdf | |
| dc.identifier | archive/lib.dr.iastate.edu/chem_pubs/112/ | |
| dc.identifier.articleid | 1111 | |
| dc.identifier.contextkey | 7876382 | |
| dc.identifier.s3bucket | isulib-bepress-aws-west | |
| dc.identifier.submissionpath | chem_pubs/112 | |
| dc.identifier.uri | https://dr.lib.iastate.edu/handle/20.500.12876/14423 | |
| dc.language.iso | en | |
| dc.source.bitstream | archive/lib.dr.iastate.edu/chem_pubs/112/0-2015_Stanley_LicenseRhodiumCatalyzed.pdf|||Fri Jan 14 18:44:44 UTC 2022 | |
| dc.source.bitstream | archive/lib.dr.iastate.edu/chem_pubs/112/2015_Stanley_RhodiumCatalyzed.pdf|||Fri Jan 14 18:44:46 UTC 2022 | |
| dc.source.uri | 10.1021/acs.orglett.5b02559 | |
| dc.subject.disciplines | Chemistry | |
| dc.title | Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes | |
| dc.type | article | |
| dc.type.genre | article | |
| dspace.entity.type | Publication | |
| relation.isAuthorOfPublication | 06a36bbf-c631-47ba-acf0-be4aea920757 | |
| relation.isOrgUnitOfPublication | 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11 |