Dual c–h functionalization of n-aryl amines & development of novel hydrogen bonding catalysts

The development of highly efficient synthetic methods resulting in multiple bond formation to generate complex molecules in a single step is highly desirable. We have recently reported an efficient and alternative oxidative Povarov approach, along with its application in synthesis of polycyclic amines. This reaction features dual C–H activation, which in addition to α-functionalization of C(sp3)–H bonds of amines, simultaneously results in the functionalization of an ortho C(sp2)–H bond of the aryl ring. A classical Povarov approach to synthesize such polycyclic amines would require complex starting materials. A wide range of N-aryl amines readily underwent the oxidative Povarov reaction to give polycyclic amines in moderate to good yield and diastereomeric ratios. Moreover, a broad range of dienophiles tested also gave the desired product in moderate to good yields and diastereomeric ratios. Enzymes achieve nearly catalytic perfection through the arrangement of specific functional groups in space. We thought whether this effect could be exploited in the development of more efficient asymmetric catalysts that operate via H-bonding. In this context, I developed the synthesis of chiral multifunctional polythioureas, which operates via an intramolecular H-bonding.

Contributors dc:contributor

• Sanchawala, Abbas I., 1988- (author)
• Baum, Jean (chair)
• Seidel, Daniel (internal member)
• Williams, Lawrence J. (internal member)
• Zhang, Xumu (internal member)
• Rutgers University
• Graduate School - New Brunswick

• Chemistry and Chemical Biology
• Hydrogen bonding
• Catalysts

Statement dc:rights

• The author owns the copyright to this work.

Language dc:language

eng

Identifier

rutgers-lib:45451
ETD_5839

OAI identifier oai:identifier

oai:example.org:rutgers-lib:45451