Synthesis of Saturated Building Blocks: From Conformationally Rigid Bicycles to Alkyl Boronates

Conformational rigidification is an established strategy in the field of drug discovery as it improves the pharmacological profile of drug candidates. Cyclobutanes and cyclopropanes gain popularity in drug discovery due to their rigid structure. However, cyclopentane and cyclohexane rings are flexible. To rigidify the conformation of these medium size ring systems, bicyclo[2.1.1]-hexane systems and [2]ladderane systems were synthesized and further functionalized using [2+2]-cycloaddition, Wolff rearrangement, C-H functionalization reactions. Taking inspiration from the diazo intermediates used in the Wolff rearrangement reaction, a deaminative cross-coupling reaction of alkyl nitroso carbamates was also developed. Due to strong C-N bond, cross coupling of alkyl amines are difficult. To circumvent this problem, a metal free cross coupling reaction between alkyl nitroso carbamates and boronic acids was developed to synthesize complex secondary boronates. Later, the deamination strategy was also used for palladium catalysed heck type coupling reactions.

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