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Studies towards a catalytic asymmetric isomerization of manganese complexed alkynes to allenes using chiral bases

The conversion of alkynyl carbonyls to allenyl carbonyls via manganese mediated coordination followed by a base-catalyzed isomerization was carried out using a range of chiral and achiral amine bases. Chiral amidine and chiral DBU derivatives were synthesized to carry out the isomerization enantioselectively. We employed HPLC equipped with a chiral column to determine the enantiomeric excess. We also proved that the mechanism of that the manganese-coordinated alkyne/allene rearrangement reaction involved an intermediate cumenolate. It was also confirmed that amine base with pKa lower than that of DBU (pKa = 13.6) would not carry out the isomerization. Alkoxy base were also used in isomerization and the mechanism was also investigated. / by Chang He. / Thesis (M.S.)--Florida Atlantic University, 2009. / Includes bibliography. / Electronic reproduction. Boca Raton, Fla., 2009. Mode of access: World Wide Web.

Identiferoai:union.ndltd.org:fau.edu/oai:fau.digital.flvc.org:fau_2974
ContributorsHe, Chang., Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
PublisherFlorida Atlantic University
Source SetsFlorida Atlantic University
LanguageEnglish
Detected LanguageEnglish
TypeText, Electronic Thesis or Dissertation
Formatxiii, 111 p. : ill. (some col.)., electronic
Rightshttp://rightsstatements.org/vocab/InC/1.0/

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