eprintid: 7709
rev_number: 4
userid: 6
dir: disk0/00/00/77/09
datestamp: 2011-11-10 19:42:57
lastmod: 2016-11-15 13:42:51
status_changed: 2011-11-10 19:42:57
type: thesis_degree
metadata_visibility: show
contact_email: xid4@pitt.edu
item_issues_count: 0
eprint_status: archive
creators_name: Ding, Xiaoyuan
creators_email: xid4@pitt.edu
creators_id: XID4
title: Synthesis of Quasienantiomeric Fluorous-Tagged Oxazolidinonesand Application in Alkylation and syn-Aldol Reactions
ispublished: unpub
divisions: sch_as_chemistry
full_text_status: public
keywords: oxazolidinones
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.
date: 2006-06-29
date_type: completed
institution: University of Pittsburgh
refereed: TRUE
etdcommittee_type: committee_chair
etdcommittee_type: committee_member
etdcommittee_type: committee_member
etdcommittee_name: Curran, Dennis
etdcommittee_name: Schafmeister, Chris
etdcommittee_name: Wilcox, Craig
etdcommittee_email: curran@pitt.edu
etdcommittee_email: meister@pitt.edu
etdcommittee_email: daylite@pitt.edu
etdcommittee_id: CURRAN
etdcommittee_id: MEISTER
etdcommittee_id: DAYLITE
etd_defense_date: 2006-01-29
etd_approval_date: 2006-06-29
etd_submission_date: 2006-04-28
etd_access_restriction: immediate
etd_patent_pending: FALSE
assigned_doi: doi:10.5195/pitt.etd.2011.7709
thesis_type: thesis
degree: MS
committee: Dennis Curran (curran@pitt.edu) - Committee Chair
committee: Chris Schafmeister (meister@pitt.edu) - Committee Member
committee: Craig Wilcox (daylite@pitt.edu) - Committee Member
etdurn: etd-04282006-130951
other_id: http://etd.library.pitt.edu/ETD/available/etd-04282006-130951/
other_id: etd-04282006-130951
citation:   Ding, Xiaoyuan  (2006) Synthesis of Quasienantiomeric Fluorous-Tagged Oxazolidinonesand Application in Alkylation and syn-Aldol Reactions.  Master's Thesis, University of Pittsburgh.    (Unpublished)  
document_url: http://d-scholarship-dev.library.pitt.edu/7709/1/thesisofxiaoyuan.pdf