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Dissertation
Diastereoselective reductions of cyclic N-diphenylphosphinyl imines to N-diphenylphosphinyl amines using amine boranes: studies directed towards the synthesis and reaction of phosphinyl enamides
Doctor of Philosophy (Ph.D.), Drexel University
2000
DOI:
https://doi.org/10.17918/00005359
Abstract
Part I. Various amine boranes were used in the reduction of substituted cyclic N-diphenylphosphinyl imines to the corresponding N-diphenylphosphinyl amines, which represent protected primary amines. t-Butylamine borane in methanol appeared to be the most efficient amine borane reagent to accomplish diastereoselective reductions. For reductions of 3- and 4-substituted cyclohexyl systems, this reagent showed a strong preference for axial attack to give the equatorial (trans) isomers. Results with 2-substituted cyclohexyl systems varied depending on the substituent, although all showed a preference for the trans isomer. Cyclopentyl and bicyclic imines were attacked from the less sterically hindered face. Part II. Attempts to synthesize alkylphosphinyl imines from oximes using diphenylchlorophosphine and triethylamine at -50° C led instead to the corresponding phosphinyl enamides, which are apparently more thermodynamically stable. Attention was then turned to the utilization of the phosphinyl enamides in Diels-Alder cycloaddition reactions. This section describes the results.
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Details
- Title
- Diastereoselective reductions of cyclic N-diphenylphosphinyl imines to N-diphenylphosphinyl amines using amine boranes
- Creators
- Susan A. Rutkowsky
- Contributors
- Robert O. Hutchins (Advisor) - Drexel University, Drexel University (1970-)
- Awarding Institution
- Drexel University
- Degree Awarded
- Doctor of Philosophy (Ph.D.)
- Publisher
- Drexel University; Philadelphia, Pennsylvania
- Number of pages
- xvii, 194 pages
- Resource Type
- Dissertation
- Language
- English
- Academic Unit
- College of Arts and Sciences; Drexel University
- Other Identifier
- 991021889054104721