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  Catalytic Asymmetric Hydroalkoxylation of C–C Multiple Bonds

Kennemur, J. L., Maji, R., Scharf, M. J., & List, B. (2021). Catalytic Asymmetric Hydroalkoxylation of C–C Multiple Bonds. Chemical Reviews, 121(24), 14649-14681. doi:10.1021/acs.chemrev.1c00620.

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Kennemur-Maji-Scharf-List.pdf (Publisher version), 6MB
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 Creators:
Kennemur, Jennifer L.1, Author              
Maji, Rajat1, Author              
Scharf, Manuel J.1, Author              
List, Benjamin1, Author              
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1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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 Abstract: Asymmetric hydroalkoxylation of alkenes constitutes a redox-neutral and 100% atom-economical strategy toward enantioenriched oxygenated building blocks from readily available starting materials. Despite their great potential, catalytic enantioselective additions of alcohols across a C–C multiple bond are particularly underdeveloped, especially compared to other hydrofunctionalization methods such as hydroamination. However, driven by some recent innovations, e.g., asymmetric MHAT methods, asymmetric photocatalytic methods, and the development of extremely strong chiral Brønsted acids, there has been a gratifying surge of reports in this burgeoning field. The goal of this review is to survey the growing landscape of asymmetric hydroalkoxylation by highlighting exciting new advances, deconstructing mechanistic underpinnings, and drawing insight from related asymmetric hydroacyloxylation and hydration. A deep appreciation of the underlying principles informs an understanding of the various selectivity parameters and activation modes in the realm of asymmetric alkene hydrofunctionalization while simultaneously evoking the outstanding challenges to the field moving forward. Overall, we aim to lay a foundation for cross-fertilization among various catalytic fields and spur further innovation in asymmetric hydroalkoxylations of C–C multiple bonds.

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Language(s): eng - English
 Dates: 2021-07-142021-12-032021-12-22
 Publication Status: Published in print
 Pages: 33
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.chemrev.1c00620
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Title: Chemical Reviews
  Abbreviation : Chem. Rev.
Source Genre: Journal
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Publ. Info: Washington, DC. : American Chemical Society
Pages: - Volume / Issue: 121 (24) Sequence Number: - Start / End Page: 14649 - 14681 Identifier: ISSN: 0009-2665
CoNE: https://pure.mpg.de/cone/journals/resource/954925389243