Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/100556
Title: Gold-catalyzed cycloisomerization of 1,6,8-dienyne carbonates and esters to cis-cyclohepta-4,8-diene-fused pyrrolidines
Authors: Sally
Berry, Stuart Neil
Chan, Philip Wai Hong
Rao, Weidong
Keywords: DRNTU::Science::Physics::Atomic physics::Solid state physics
Issue Date: 2014
Source: 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.
Series/Report no.: Chemistry - a European journal
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.
URI: https://hdl.handle.net/10356/100556
http://hdl.handle.net/10220/24142
ISSN: 0947-6539
DOI: 10.1002/chem.201402500
Rights: © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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