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Chemistry

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1,2-Diazetidine As A New Amidomethylative Reagent To Control The Selectivity For The Synthesis Of N-Heterocycles And Ru(Ii)-Catalyzed Enantioselective Hydroarylation To Form Chromane Derivatives, Chaminda Lakmal Hetti Handi Dec 2021

1,2-Diazetidine As A New Amidomethylative Reagent To Control The Selectivity For The Synthesis Of N-Heterocycles And Ru(Ii)-Catalyzed Enantioselective Hydroarylation To Form Chromane Derivatives, Chaminda Lakmal Hetti Handi

Theses and Dissertations

1,2-Diazetidine is a four-membered ring heterocyclic compound which has two adjacent nitrogen atoms. However, the syntheses of C-unsubstituted 1,2-diazetidines are rarely reported in the literature. C-unsubstituted 1,2-diazetidines were synthesized through an operationally simple intermolecular vicinal disubstitution reaction between 1,2-dibromoethane and hydrazine with N-arylsulfonyl as the protecting group. Several different types of C-unsubstituted 1,2-diazetidines derivatives were synthesized with either two of the same or two different N-arylsulfonyl groups. The electronic and steric properties were analyzed using Raman spectroscopy and computational calculations. Then, several synthetic applications were demonstrated with 1,2-ditosyl-1,2-diazetidine (DTD). As a synthetic application, a nucleophilic ring-opening reaction of the diazetidine …


Asymmetric Synthesis Of All-Carbon Α-Aryl Quaternary Carbonyl Compounds By Palladium-Catalyzed Asymmetric Allylic Alkylation (Pd-Aaa) And Their Application To The Synthesis Of Biologically Important 3,3′-Disubstituted Oxindole And Α-Disubstituted Quaternary Β-Lactone Frameworks, Md. Sharif Al Asad Aug 2015

Asymmetric Synthesis Of All-Carbon Α-Aryl Quaternary Carbonyl Compounds By Palladium-Catalyzed Asymmetric Allylic Alkylation (Pd-Aaa) And Their Application To The Synthesis Of Biologically Important 3,3′-Disubstituted Oxindole And Α-Disubstituted Quaternary Β-Lactone Frameworks, Md. Sharif Al Asad

Theses and Dissertations

The development of catalytic, enantioselective methods for the construction of all-carbon quaternary stereocenters is an outstanding achievement in the recent history of organic chemistry. The palladium-catalyzed asymmetric allylic alkylation (Pd-AAA) reaction has played a key role in creating such stereocenters and has allowed researchers to synthesize a vast number of biologically potent natural products. However, synthetic methodologies to access compounds containing α-aryl groups to the quaternary carbon stereocenters are still rare. The increasing appearance of these all-carbon α-aryl quaternary stereocenters in a growing number of biologically active natural products and pharmaceutical agents creates a pressing need for the ability to …