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Chiral 2-aminodmap/sulfonamides And Squaramides Asbifunctional Acid/base Organocatalysts In Asymmetriccatalysis

Synthesis and evaluation of catalytic performances of novel bifunctional 2-
aminoDMAP-Thiourea/ Sulfonamide/ Squaramide organocatalysts derived from
trans-(R,R)-cyclohexane-1,2-diamine forms the main goal of this thesis. For this
purpose, direct selective mono-N-pyridilization of trans-(R,R)-cyclohexane-1,2-
diamine via Pd and Cu catalysis is described successfully first. Facile preparation of
chiral 2-aminoDMAP core catalaphore led to the development of various 2-
aminoDMAP- Thiourea/ Sulfonamides/ Squaramides as bifunctional acid/base
organocatalyst libraries (most in two-steps overall) which showed good results in
asymmetric conjugate addition of 1,3-dicarbonyls to trans-(&beta / )-nitrostyrene.
Enantiomeric excesses (ee) up to 93% were attained.

Identiferoai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/12613444/index.pdf
Date01 August 2011
CreatorsIsik, Murat
ContributorsTanyeli, Cihangir
PublisherMETU
Source SetsMiddle East Technical Univ.
LanguageEnglish
Detected LanguageEnglish
TypePh.D. Thesis
Formattext/pdf
RightsTo liberate the content for public access

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