SYNTHESIS Best Paper Award 2016: Enantioselective Vicinal Diacetoxylation of Alkenes under Chiral Iodine(III) Catalysis

Kilian Muñiz highlights his award-winning paper on the iodine(III)-catalyzed enantioselective vicinal diacetoxylation of alkenes in an interview with SYNFORM.

The idea of exploring chiral non-racemic iodine(III) reagents to achieve vicinal dioxygenation of alkenes was initially conceived by Thomas Wirth in pioneering studies from the 1990s and extended by Morifumi Fujita. The Muñiz group initially became interested in these types of reagents within their work on the related 1,2-diamination of alkenes and suddenly found themselves involved in the question of how to pursue asymmetric reactions catalytic in iodine(III). Together with Kazuaki Ishihara they have explored the working mode of related catalysts and identified supramolecular hydrogen bonding as a powerful tool for the design of aryliodine(III) catalysts. 

The results reported in the SYNTHESIS paper are based on a postdoctoral stay of Thorsten Wöste, who was able to develop well-balanced conditions that use electrophilic fluorine reagents for the selective oxidation of the iodine center and to prevent any possible achiral background reaction. The publication also devotes some effort to understanding the underlying mechanistic pathways that are involved in the diacetoxylation reaction.

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