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TitleNew approaches to asymmetric nucleophilic catalysis and the development of redox-neutral reaction cascades
NameDe, Chandra Kanta (author), Seidel, Daniel (chair), Warmuth, Ralf (internal member), Hultzsch, Kai C (internal member), Hughes, Gregory (outside member), Rutgers University, Graduate School - New Brunswick,
Degree Date2011-10
Date Created2011
SubjectChemistry and Chemical Biology,
Nucleophilic reactions
DescriptionA new concept for nucleophilic catalysis has been developed and this strategy was successfully applied to the kinetic resolution of benzylic amines and propargylic
amines. The first catalytic enantioselective desymmetrization of meso-1,2-diarylaminoethanes has been introduced. A combination of nucleophilic catalyst
DMAP and hydrogen bonding catalyst afforded the monoacylated products in good yields and good to excellent enantioselectivity. A catalytic enantioselective Steglich rearrangement reaction has also been developed using our dual catalytic approach for
nucleophilic catalysis. A novel catalytic enantioselective transformation between azlactones and isoquinolines has been developed. To the best of our knowledge, this
type of functionalization of isoquinolines with azlactones is unprecedented. A redox neutral reaction cascade that involves the functionalization of the relatively
unactivated C–H bond α to the nitrogen of cyclic amines has been developed. This transformation represents a fast route to synthetically useful aminal building blocks.
A mechanistically unique 2,3-annulation of indole based on the tert-amino effect 1,5-hydride shift/ring closure sequence has been shown. This redox-neutral C–H functionalization leads to a new class of ring fused indolobenzazepines and features short reaction times. Apart from indole, the substrate scope includes pyrroles and 1,2-diarylhydrazines.
amines. The first catalytic enantioselective desymmetrization of meso-1,2-diarylaminoethanes has been introduced. A combination of nucleophilic catalyst
DMAP and hydrogen bonding catalyst afforded the monoacylated products in good yields and good to excellent enantioselectivity. A catalytic enantioselective Steglich rearrangement reaction has also been developed using our dual catalytic approach for
nucleophilic catalysis. A novel catalytic enantioselective transformation between azlactones and isoquinolines has been developed. To the best of our knowledge, this
type of functionalization of isoquinolines with azlactones is unprecedented. A redox neutral reaction cascade that involves the functionalization of the relatively
unactivated C–H bond α to the nitrogen of cyclic amines has been developed. This transformation represents a fast route to synthetically useful aminal building blocks.
A mechanistically unique 2,3-annulation of indole based on the tert-amino effect 1,5-hydride shift/ring closure sequence has been shown. This redox-neutral C–H functionalization leads to a new class of ring fused indolobenzazepines and features short reaction times. Apart from indole, the substrate scope includes pyrroles and 1,2-diarylhydrazines.
NotePh. D.
NoteIncludes bibliographical references
Noteby Chandra Kanta De
Genretheses
Persistent URLhttp://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000063392
Languageeng
CollectionGraduate School - New Brunswick Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.