Novel applications of α-diazocarbonyl compounds and enabling technologies in stereoselective synthesis
2020
α-Diazocarbonyl compounds are widely used in organic chemistry as versatile carbene
precursors which enable concise synthesis towards complex asymmetric molecules.
Due to their intrinsic highly energetic nature, flow technology can be applied to ensure
safer, scalable and efficient protocols. Other modern enabling tools such as Design of
Experiment (DoE) and online analysis, provide great advantages to achieve faster
analysis and optimisations of chemical transformations.
In the first part of this work, α-diazocarbonyl compounds have been used in the
enantioselective synthesis of novel trans-indolines.1
The synthesis of the diazo precursors, previously investigated in batch, was translated
into a flow system and optimised following a DoE-approach. Moreover, highly Lewis
acidic boranes were found to enable related α-diazocarbonyl compounds to undergo a
metal-free transfer/rearrangement cascade reaction towards asymmetric benzofuran-
3H-ones.2
The focus in the final part of this work was on the development of a faster analytical
method for an accelerated optimisation of stereoselective reactions. The reactions were
performed in a continuous flow electrochemical reactor directly coupled to a 2D‐HPLC
for immediate online analysis, which allowed a fast screening of reaction conditions using
DoE.3
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