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Catalytic Reductive Pinacol-Type Rearrangement of Unactivated 1,2-Diols through a Concerted, Stereoinvertive Mechanism

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Drosos,  Nikolaos
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cheng,  Gui-Juan
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Özkal,  Erhan
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cacherat,  Bastien
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Thiel,  Walter
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Morandi,  Bill
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Drosos, N., Cheng, G.-J., Özkal, E., Cacherat, B., Thiel, W., & Morandi, B. (2017). Catalytic Reductive Pinacol-Type Rearrangement of Unactivated 1,2-Diols through a Concerted, Stereoinvertive Mechanism. Angewandte Chemie International Edition, 56(43), 13377-13381. doi:10.1002/anie.201704936.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002E-9D50-0
Abstract
A catalytic pinacol-type reductive rearrangement reaction of internal 1,2-diols is reported herein. Several scaffolds not usually amenable to pinacol-type reactions, such as aliphatic secondary–secondary diols, undergo the transformation well without the need for prefunctionalization. The reaction uses a simple boron catalyst and two silanes and proceeds through a concerted, stereoinvertive mechanism that enables the preparation of highly enantiomerically enriched products. Computational studies have been used to rationalize the preference for migration over direct deoxygenation.