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Synthesis of Quasienantiomeric Fluorous-Tagged Oxazolidinonesand Application in Alkylation and syn-Aldol Reactions

Ding, Xiaoyuan (2006) Synthesis of Quasienantiomeric Fluorous-Tagged Oxazolidinonesand Application in Alkylation and syn-Aldol Reactions. Master's Thesis, University of Pittsburgh. (Unpublished)

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Abstract

Evans' oxazolidinones are among the most well-established and extensively used chiral auxiliaries for stoichiometric asymmetric methods in total synthesis. The most common applications are á-alkylation and syn-aldol reactions, which build either enantiomers or diastereomers containing flexible function groups for further elaboration. Fluorous quasiracemic synthesis involves synthesis of both enantiomers of a target compound in a single synthesis by implementation of a fluorous tagging strategy. Here, two different fluorous-tagged oxazolidinones were synthesized in an efficientt synthetic strategy. Preliminary alkylation and aldol condensation of the fluorous-tagged imides derived from the corresponding oxazolidinones were carried out and compared with the non fluorous-tagged imide in the aspect of yield and diastereomer ratios. The alkylation and aldol reactions of the quasiracemic mixture were conducted and the resultant crude products were subjected to HPLC analysis.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Ding, Xiaoyuanxid4@pitt.eduXID4
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairCurran, Denniscurran@pitt.eduCURRAN
Committee MemberSchafmeister, Chrismeister@pitt.eduMEISTER
Committee MemberWilcox, Craigdaylite@pitt.eduDAYLITE
Date: 29 June 2006
Date Type: Completion
Defense Date: 29 January 2006
Approval Date: 29 June 2006
Submission Date: 28 April 2006
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: oxazolidinones
Other ID: http://etd.library.pitt.edu/ETD/available/etd-04282006-130951/, etd-04282006-130951
Date Deposited: 10 Nov 2011 19:42
Last Modified: 15 Nov 2016 13:42
URI: http://d-scholarship.pitt.edu/id/eprint/7709

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