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

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.

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 Creators:
Drosos, Nikolaos1, Author              
Cheng, Gui-Juan2, Author              
Özkal, Erhan1, Author              
Cacherat, Bastien1, Author              
Thiel, Walter2, Author              
Morandi, Bill1, Author              
Affiliations:
1Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040309              
2Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              

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Free keywords: boron; diols; pinacol rearrangement; silanes; stereoselectivity
 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.

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Language(s): eng - English
 Dates: 2017-05-132017-07-262017-09-182017-10-16
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201704936
 Degree: -

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Title: Angewandte Chemie International Edition
  Other : Angew. Chem., Int. Ed.
  Other : Angew. Chem. Int. Ed.
  Other : Angewandte Chemie, International Edition
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 56 (43) Sequence Number: - Start / End Page: 13377 - 13381 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851