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Chiral beta-Amino Sulfenates: Synthetic Access and Diastereoselective Alkylation

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dc.contributor.advisor Schwan, Adrian Findlay, Joseph 2019-05-15T12:48:16Z 2019-05-15T12:48:16Z 2019-05 2019-05-10 2019-05-15
dc.description.abstract Research into a new family of chiral sulfenates containing a β-substituted, N-protected β- amino functionality, derived from amino acids, has been extended in this investigation for its diastereoselective alkylation reactions of sulfenates. Two L-phenylalanine derived precursors to the in-situ generation of a β-amino sulfenate were prepared by multiple convergent pathways, and each sulfenate liberation method was evaluated by alkylation with BnBr for both its diastereoselection, and overall sulfoxide yield. It was demonstrated that sulfenate liberation from the β-sulfinyl ester proved to be a superior method when employed with the base LiHMDS. Evaluation of this method by variation of temperature, showed no significant variance in dr’s, but affected yields depending on the electrophile utilized. Other β-amino sulfenates derived from N- Boc protected D-phenylalanine, L-valine, L-alanine, as well as Cbz protected L-phenylalanine were also evaluated by alkylation with BnBr and showed mixed yields ranging from 58-90% and yields generally around 20:80. en_US
dc.language.iso en en_US
dc.subject Sulfenates en_US
dc.subject Sulfoxides en_US
dc.subject Asymmetric en_US
dc.subject Synthesis en_US
dc.subject Sulfur en_US
dc.title Chiral beta-Amino Sulfenates: Synthetic Access and Diastereoselective Alkylation en_US
dc.type Thesis en_US Chemistry en_US Master of Science en_US Department of Chemistry en_US
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