Journal article

Control of absolute stereochemistry in transition-metal-catalyzed hydrogen borrowing reactions

Abstract:: Hydrogen borrowing catalysis represents a powerful method for the alkylation of amine or enolate nucleophiles with unactivated alcohols. This approach relies upon a catalyst which can mediate a strategic series of redox events, enabling the formation of C–C and C–N bonds and producing water as the sole by‐product. In the majority of cases these reactions have been employed to target achiral or racemic products. In contrast, the focus of this minireview is upon hydrogen borrowing catalyzed reactions in which the absolute stereochemical outcome of the process can be controlled. Asymmetric hydrogen borrowing catalysis is rapidly emerging as a powerful approach for the synthesis of enantioenriched amine and carbonyl containing products and examples involving both C–N and C–C bond formation are presented. A variety of different approaches are discussed including use of chiral auxiliaries, asymmetric catalysis and enantiospecific processes.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Kwok, T., Hoff, O., Armstrong, R. J., & Donohoe, T. J. (2020). Control of absolute stereochemistry in transition-metal-catalyzed hydrogen borrowing reactions. Chemistry - A European Journal , 26(57), 12912–12926.

MLA Style

Kwok, T., et al. “Control of Absolute Stereochemistry in Transition-Metal-Catalyzed Hydrogen Borrowing Reactions.” Chemistry - A European Journal , vol. 26, no. 57, Wiley, 2020, pp. 12912–26.

Chicago Style

Kwok, T, O Hoff, RJ Armstrong, and TJ Donohoe. 2020. “Control of Absolute Stereochemistry in Transition-Metal-Catalyzed Hydrogen Borrowing Reactions.” Chemistry - A European Journal 26 (57): 12912–26.
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Files:: Kwok_et_al_2020_Control_of_absolute.pdf

(Preview, Accepted manuscript, 2.8MB, Terms of use)

Publisher copy:: 10.1002/chem.202001253

Authors

+ Kwok, T More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Chemistry Research Laboratory
Role:: Author

+ Hoff, O More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Chemistry Research Laboratory
Role:: Author

+ Armstrong, RJ More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Chemistry Research Laboratory
Role:: Author

+ Donohoe, TJ More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

Publisher:: Wiley
Journal:: Chemistry - A European Journal More from this journal
Volume:: 26
Issue:: 57
Pages:: 12912-12926
Publication date:: 2020-09-11
Acceptance date:: 2020-04-06
DOI:: 10.1002/chem.202001253
EISSN:: 1521-3765
ISSN:: 0947-6539
Pmid:: 32297370

Language:: English
Keywords:: enantioselective

FFR

amines

hydrogen borrowing catalysis

asymmetric

enolates
Pubs id:: 1101272
Local pid:: pubs:1101272
Deposit date:: 2020-07-10

Terms of use

Copyright holder:: WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Copyright date:: 2020
Rights statement:: © 2020 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Notes:: This is the accepted manuscript version of the article. The final version is available online from Wiley at: https://doi.org/10.1002/chem.202001253

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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