Synthesis of Chiral Surfactants for Enantioselective Organic Synthesis.

<p>The first step of the synthesis of the hydrocarbon-based chiral surfactant <b>(2)</b> 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 <b>(1)</b> with bromohexadecane (2.06g, 71%). The functionalized styrene for the polymer supported chiral catalyst <b>(6)</b> was synthesized by reacting <b>(1)</b> with 4-vinylbenzyl chloride. The polymerization was carried out with 10% of the functionalized monomer <b>(5)</b> (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 <b>(3)</b> (4gm, 25%). The resulting alcohol was then esterified with (2S)-methylbutyric acid with iodine as the catalyst and the ester was characterized.</p>

Name thesis:degree_name

MS (Master of Science)

Level thesis:degree_level

Thesis - unrestricted

Discipline thesis:degree_discipline

Chemistry

Year dc:date.issued

2003

Author dc:creator

• Mondal, Kalyan

• Chiral Surfactants
• Dimethyl Leucinol
• Functionalized Monomer based on Vinylbenzyl Chlori
• Alkyl Halide
• Enantiomers
• Enantioselective
• Chemistry
• Physical Sciences and Mathematics

Statement dc:rights

• Copyright by the authors.

Repository record dc:identifier

https://dc.etsu.edu/etd/798

OAI identifier oai:identifier

oai:dc.etsu.edu:etd-1955