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Diastereoselective Synthesis of Cyclopentenes via RhII-Catalyzed C-H Insertion Directed by a Planar Chiral N-Oxazolidinoyl Iron(0) Tricarbonyl Diene Complex

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dc.contributor.advisor Paley, Robert S.
dc.contributor.author Hejna, Benjamin G.
dc.date.accessioned 2019-07-11T19:04:24Z
dc.date.available 2019-07-11T19:04:24Z
dc.date.issued 2019
dc.identifier.uri http://hdl.handle.net/10066/21533
dc.description.abstract Herein is presented a general methodology for the synthesis of cyclopentenes bearing two consecutive, diastereoselectively generated stereocenters by RhII-catalyzed C-H insertion using a planar chiral N-oxazolidinoyl iron(0) tricarbonyl diene complex as a steric directing group. The majority of this work is dedicated to designing and accessing viable substrates to undergo the aforementioned diastereomerically selective C-H insertion, as well as determination of the absolute stereochemical configuration of the enantiomerically pure product. We hypothesize that the observed stereochemical outcome is caused by the favorability of orienting the substituent on each newly-generated stereocenter away from the sterically bulky iron(0) tricarbonyl fragment. In addition to this methodology, a number of other methods are presented describing the reactivity of N-oxazolidinoyl iron(0) tricarbonyl dienes, including novel diazo transfers, mild removal of the oxazolidinone auxiliary, and diastereoselective intramolecular cyclizations, oxidative removal of the iron(0) tricarbonyl moiety, as well as steps towards electrochemical decomplexation. en_US
dc.description.sponsorship Swarthmore College. Dept. of Chemistry & Biochemistry en_US
dc.language.iso en en_US
dc.rights Full copyright to this work is retained by the student author. It may only be used for non-commercial, research, and educational purposes. All other uses are restricted.
dc.title Diastereoselective Synthesis of Cyclopentenes via RhII-Catalyzed C-H Insertion Directed by a Planar Chiral N-Oxazolidinoyl Iron(0) Tricarbonyl Diene Complex en_US
dc.rights.access No restrictions en_US


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