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Synthesis of Chiral Surfactants for Enantioselective Organic Synthesis.

The first step of the synthesis of the hydrocarbon-based chiral surfactant (2) involved the methylation of (S)-leucinol to give (2S)-N-hexadecyl-N,N-dimethyl-(1-hydroxy-4-methyl-1-pentyl)-2-ammonium bromide (2.92g, 67%). The chiral surfactant was synthesized by reacting (2S)-N,N-dimethyl-2-amino-4-methyl-1-pentanol (1) with bromohexadecane (2.06g, 71%). The functionalized styrene for the polymer supported chiral catalyst (6) was synthesized by reacting (1) with 4-vinylbenzyl chloride. The polymerization was carried out with 10% of the functionalized monomer (5) (1.26g, 70.2%), 5% cross-linking agent divinylbenzene, and 85% of styrene with AIBN as the initiator. The structure of each of the products was confirmed by using FTIR and NMR spectroscopy. The activity of the hydrocarbon surfactant and polymeric catalyst were examined by using them as additives in a standard reduction of 2-pentanone with sodium borohydride to yield (R)- and (S)-2-pentanol (3) (4gm, 25%). The resulting alcohol was then esterified with (2S)-methylbutyric acid with iodine as the catalyst and the ester was characterized.

Identiferoai:union.ndltd.org:ETSU/oai:dc.etsu.edu:etd-1955
Date11 August 2003
CreatorsMondal, Kalyan
PublisherDigital Commons @ East Tennessee State University
Source SetsEast Tennessee State University
Detected LanguageEnglish
Typetext
Formatapplication/pdf
SourceElectronic Theses and Dissertations
RightsCopyright by the authors.

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