The Use of 2-Bornanethiol for the Asymmetric Synthesis of Amines
The University of Maryland McNair Scholars Undergraduate Research Journal, 2, (2010): 209-243.
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The proposal to synthesize a camphor sulfinamide reagent using 2-bornanethiol was initiated. A novel disulfide for the synthesis of the reagent was produced through inexpensive means via three synthetic steps. Readily available (+)-camphor underwent thionation using phosphorous pentasulfide in excess. The resulting thiocamphor was reduced to camphor thiol (or 2-bornanethiol) and oxidized to yield camphor disulfide. Further investigation of the disulfide is necessary for confirmation and characterization. Oxidation followed by reaction of the purified sample of this product with ammonia and lithium amide could give camphor sulfinamide. It was determined that purification at the end of each step would help to give better results and cleaner NMR spectra to analyze. Limitations included difficulty with keeping reactions under dry conditions as well as large amounts of time required to run each reaction. From here, the purified disulfide will be used to synthesize camphor sulfinamide which could then be combined with chiral aldehydes and ketones to yield imines in high selectivity.