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theses

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.

ETD_5839

M.S.

Includes bibliographical references

by Abbas I. Sanchawala

doi:10.7282/T3057HJV

ETD graduate

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