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https://hdl.handle.net/10356/100556
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DC Field | Value | Language |
---|---|---|
dc.contributor.author | Sally | en |
dc.contributor.author | Berry, Stuart Neil | en |
dc.contributor.author | Chan, Philip Wai Hong | en |
dc.contributor.author | Rao, Weidong | en |
dc.date.accessioned | 2014-10-29T00:57:22Z | en |
dc.date.accessioned | 2019-12-06T20:24:25Z | - |
dc.date.available | 2014-10-29T00:57:22Z | en |
dc.date.available | 2019-12-06T20:24:25Z | - |
dc.date.copyright | 2014 | en |
dc.date.issued | 2014 | en |
dc.identifier.citation | Rao, W., Sally, Berry, S. N., & Chan, P. W. H. (2014). Gold-catalyzed cycloisomerization of 1,6,8-dienyne carbonates and esters to cis-cyclohepta-4,8-diene-fused pyrrolidines. Chemistry - A European journal, 20(41), 13174-13180. | en |
dc.identifier.issn | 0947-6539 | en |
dc.identifier.uri | https://hdl.handle.net/10356/100556 | - |
dc.description.abstract | A synthetic approach that provides access to cis-cyclohepta-4,8-diene-fused pyrrolidines efficiently through AuI-catalyzed cycloisomerization of 1,6,8-dienyne carbonates and esters at a low catalyst loading of 2 mol % is reported. Starting carbonates and esters with a pendant alkyl group on the terminal alkenyl carbon center were found to favor tandem 1,2-acyloxy migration/cyclopropanation followed by Cope rearrangement of the resulting cis-3-azabicyclo[3.1.0]hexane intermediate. On the other hand, substrates containing a terminal diene or starting materials in which the distal alkene moiety bears a phenyl substituent were observed to undergo competitive but reversible 1,3-acyloxy migration prior to the nitrogen-containing bicyclic ring formation. The delineated reaction mechanism also provides experimental evidence for the reversible interconversion between the oft-proposed organogold intermediates obtained in this step of the tandem process. | en |
dc.language.iso | en | en |
dc.relation.ispartofseries | Chemistry - a European journal | en |
dc.rights | © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | en |
dc.subject | DRNTU::Science::Physics::Atomic physics::Solid state physics | en |
dc.title | Gold-catalyzed cycloisomerization of 1,6,8-dienyne carbonates and esters to cis-cyclohepta-4,8-diene-fused pyrrolidines | en |
dc.type | Journal Article | en |
dc.contributor.school | School of Physical and Mathematical Sciences | en |
dc.identifier.doi | 10.1002/chem.201402500 | en |
item.fulltext | No Fulltext | - |
item.grantfulltext | none | - |
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