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Published on: November 9, 2019
Regiodivergent epoxide opening: a concept in stereoselective catalysis beyond classical kinetic resolutions and
Andreas Gansäuer1, Chun-An Fan, Florian Keller
1Kekulé-Institut für Organische Chemie und Biochemie Universität Bonn, Gerhard Domagk Str. 1, 53127 Bonn, Germany. andreas.gansaeuer@uni-bonn.de
Abstract:
An approach to highly regiodivergent epoxide openings (REOs) is presented. The very popular kinetic resolutions of epoxides and openings of meso-epoxides constitute subclasses of such REOs. REOs are attractive for parallel resolutions, double asymmetric reactions of enantiomerically enriched epoxides, and for semisynthetic applications in the functionalization of natural products. They have been notoriously difficult to realize by means of SN2 mechanisms. Our titanocene-catalyzed radical REO addresses this issue by decoupling epoxide opening and radical trapping and is firmly based on a mechanistic study of the reductive epoxide opening.
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