?url_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rft.relation=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F9913%2F&rft.title=Extension+of+ketene-mediated+asymmetric+methodology&rft.creator=Raelin%2C+Jeremy+M&rft.description=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%2C+sp-hybridized+carbon+atom+is+the+origin+of+many+of+the+chemical+transformations+availible+to+these+molecules.+Previously+in+the+Nelson+laboratory%2C+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%2C4-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.&rft.date=2006-03-20&rft.type=University+of+Pittsburgh+ETD&rft.type=PeerReviewed&rft.format=application%2Fpdf&rft.language=en&rft.identifier=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F9913%2F1%2FRaelinJM_etdPitt2005.pdf&rft.identifier=++Raelin%2C+Jeremy+M++(2006)+Extension+of+ketene-mediated+asymmetric+methodology.++Master's+Thesis%2C+University+of+Pittsburgh.++++(Unpublished)++