ORCID Profile
0000-0003-4490-9542
Current Organisation
Murdoch University
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Publisher: Royal Society of Chemistry (RSC)
Date: 18-12-2001
DOI: 10.1039/B107705H
Publisher: American Chemical Society (ACS)
Date: 27-07-2004
DOI: 10.1021/JO049576N
Abstract: Reaction of lithium enolates of simple ketones with (+/-)-phenyl vinyl sulfoxide has potential for the convergent construction of complex fused ring systems containing a bicyclo[n.2.0]alkan-1-ol. The formation of sulfinylbicyclo[4.2.0]octan-1-ols 1-3 from the lithium enolate of cyclohexanone with (+/-)-phenyl vinyl sulfoxide or (R)-(+)-p-tolyl vinyl sulfoxide 18 was used to probe the mode of this novel cyclization reaction. Using phenyl vinyl sulfoxide, variations in the reaction lighting and solvent were investigated, in conjunction with radical trapping (TEMPO) and isotope labeling (deuterium) experiments. Cyclization to form sulfinylbicyclooctanols 1-3 is likely to proceed via an intermediate that ring closes to the bicycloalkanol anion 11 and was presently favored by the use of solvents such as THF or DME.
Publisher: Elsevier BV
Date: 05-2011
Publisher: CSIRO Publishing
Date: 2005
DOI: 10.1071/CH04288
Abstract: Bicyclooctanols 3 and 4 were formed with control of the stereochemistry at C8 by using an aluminium enolate of cyclohexanone in 1,2-dimethoxyethane. Bicyclooctanols 1 and 3 were stable towards aqueous hydrochloric acid for short times ( 3.5 h), and ring open to a diastereomeric mix of monoalkylated 5 under protic or aprotic conditions in the presence of base (NaOH or lithium diisopropylamide). The rate of ring opening appears to be dependent on reaction temperature. Bicyclooctanols 1, 3, and 4 displayed remarkable stability when heated at reflux in benzene, whereas use of ethanol prompted stereoselective ring opening of 1 and 3 to give in idual diastereomers of monoalkylated 5 and ring opening of 4 to give a 50 : 50 mix of diastereomers of 5. This unexpected result was attributed to the stereochemistry of the bicyclooctanol and placement of hydrogen-bonding sites.
Publisher: Wiley
Date: 09-10-2002
DOI: 10.1002/POC.542
Publisher: Georg Thieme Verlag KG
Date: 13-07-2005
Publisher: Elsevier BV
Date: 2000
Publisher: American Chemical Society (ACS)
Date: 27-02-2013
DOI: 10.1021/IE3024824
No related grants have been discovered for Catherine Rowen.