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Cyclic Phosphine Oxides and Phosphinamides from Di-Grignard Reagents and Phosphonic Dichlorides: Modular Access to Annulated Phospholanes

Gregson, Aaron M.; Wales, Steven M; Bailey, Stephen J.; Willis, Anthony; Keller, Paul

Description

The reaction between 1,4-di-Grignard reagents and phosphonous(III) dichlorides is a classical method for the direct synthesis of phospholanes. Reported here is an extension of this approach to the preparation of value-added, annulated phospholane oxides, achieved through the combination of carbocyclic-fused di-Grignard reagents and readily available phosphonic(V) dichlorides. The procedure is amenable to (benz)annulation at both the 2,3- and 3,4-positions of the phospholane ring, and a variety...[Show more]

dc.contributor.authorGregson, Aaron M.
dc.contributor.authorWales, Steven M
dc.contributor.authorBailey, Stephen J.
dc.contributor.authorWillis, Anthony
dc.contributor.authorKeller, Paul
dc.date.accessioned2016-06-14T23:20:17Z
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/103292
dc.description.abstractThe reaction between 1,4-di-Grignard reagents and phosphonous(III) dichlorides is a classical method for the direct synthesis of phospholanes. Reported here is an extension of this approach to the preparation of value-added, annulated phospholane oxides, achieved through the combination of carbocyclic-fused di-Grignard reagents and readily available phosphonic(V) dichlorides. The procedure is amenable to (benz)annulation at both the 2,3- and 3,4-positions of the phospholane ring, and a variety of aliphatic, cyclic and aryl P-electrophiles are tolerated in reasonable to excellent yields.
dc.publisherAmerican Chemical Society
dc.sourceJournal of Organic Chemistry
dc.titleCyclic Phosphine Oxides and Phosphinamides from Di-Grignard Reagents and Phosphonic Dichlorides: Modular Access to Annulated Phospholanes
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume80
dc.date.issued2015
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationU3488905xPUB6141
local.type.statusPublished Version
local.contributor.affiliationGregson, Aaron M., University of Wollongong
local.contributor.affiliationWales, Steven M, University of Wollongong
local.contributor.affiliationBailey, Stephen J., University of Wollongong
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationKeller, Paul, University of Wollongong
local.description.embargo2037-12-31
local.bibliographicCitation.issue19
local.bibliographicCitation.startpage9774
local.bibliographicCitation.lastpage9780
local.identifier.doi10.1021/acs.joc.5b01476
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2016-06-14T08:47:27Z
local.identifier.scopusID2-s2.0-84942869869
CollectionsANU Research Publications

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