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  Boron-Catalyzed Regioselective Deoxygenation of Terminal 1,2-Diols to 2-Alkanols Enabled by the Strategic Formation of a Cyclic Siloxane Intermediate

Drosos, N., & Morandi, B. (2015). Boron-Catalyzed Regioselective Deoxygenation of Terminal 1,2-Diols to 2-Alkanols Enabled by the Strategic Formation of a Cyclic Siloxane Intermediate. Angewandte Chemie International Edition, 54(30), 8814-8818. doi:10.1002/anie.201503172.

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 Creators:
Drosos, Nikolaos1, Author              
Morandi, Bill1, Author              
Affiliations:
1Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040309              

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Free keywords: EFFICIENT KINETIC RESOLUTION; FRUSTRATED LEWIS PAIRS; B(C6F5)(3)-CATALYZED HYDROSILYLATION; ASYMMETRIC HYDROGENATION; SELECTIVE DEOXYGENATION; SUGAR ALCOHOLS; ALKYL ETHERS; REDUCTION; DIOLS; DEOXYDEHYDRATIONChemistry; boron; cyclic intermediates; deoxygenation; diols; silanes;
 Abstract: The selective deoxygenation of polyols is a frontier in our ability to harness the stereochemical and structural complexity of natural and synthetic feedstocks. Herein, we describe a highly active and selective boron-based catalytic system for the selective deoxygenation of terminal 1,2-diols at the primary position, a process that is enabled by the transient formation of a cyclic siloxane. The method provides an ideal complement to well-known catalytic asymmetric reactions to prepare synthetically challenging chiral 2-alkanols in nearly perfect enantiomeric excess, as illustrated in a short synthesis of the anti-inflammatory drug (R)-lisofylline.

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Language(s): eng - English
 Dates: 2015-07-20
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: 000358051600045
DOI: 10.1002/anie.201503172
 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: 54 (30) Sequence Number: - Start / End Page: 8814 - 8818 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851