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Extension of ketene-mediated asymmetric methodology

Raelin, Jeremy M (2006) Extension of ketene-mediated asymmetric methodology. Master's Thesis, University of Pittsburgh. (Unpublished)

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Ketenes are molecules containing a carbonyl group connected to an alkylidene group by way of a double bond (a pi-bond). The electrophilic nature of ketenes at their center, sp-hybridized carbon atom is the origin of many of the chemical transformations availible to these molecules. Previously in the Nelson laboratory, ketenes had been successfully employed in the acyl halide-aldehyde cyclocondensation (AAC) reaction. Both Lewis acid- and Lewis base-catalyzed AAC processes provide access to optically active 3,4-disubstituted-syn-2-oxetanones. The work described herein employs ketene in the Lewis base-catalyzed AAC reaction in an attempt to improve and expand the general utility of this reaction technology. This improved AAC methodology was then applied in the total synthesis of the natural product motuporin. Ketene was subsequently employed in the development of a novel ketene-Claisen rearrangement.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Raelin, Jeremy Mjmr45@pitt.eduJMR45
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairNelson, Scott Gsgnelson@pitt.eduSGNELSON
Committee MemberWilcox, Craig Sdaylite@pitt.eduDAYLITE
Committee MemberWipf, Peterpwipf@pitt.eduPWIPF
Date: 20 March 2006
Date Type: Completion
Defense Date: 5 December 2005
Approval Date: 20 March 2006
Submission Date: 1 December 2005
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: 2-oxetanone; AAC; acyl-halide aldehyde cyclocondensation; beta-lactone; Claisen; ester enolate Claisen; ketene; lactone; motuporin
Other ID:, etd-12012005-162855
Date Deposited: 10 Nov 2011 20:07
Last Modified: 15 Nov 2016 13:52


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