Journal article

Bifunctional Iminophosphorane Superbases Enable the Highly Enantioselective Sulfa-Michael Addition to Fully Substituted Cyclopropene Carboxylic Acid Derivatives

Abstract:: The metal-free catalytic enantioselective intermolecular conjugate addition of alkyl thiols to unactivated β-substituted cyclopropene carboxylic acid derivatives has been developed. High enantiomeric excesses and yields were consistently achieved across a broad range of thiol pronucleophiles and fully substituted cyclopropene electrophiles under mild reaction conditions, enabled by a novel tert-leucine-derived amide-containing bifunctional iminophosphorane (BIMP) catalyst. Additionally, lowering the catalyst loading to 5.0 mol % was possible and allowed the reaction to be carried out on a gram scale.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Yuan, K., Ristache, A. I., Kosc, S. M., Crumpton, A., & Dixon, D. J. (2025). Bifunctional Iminophosphorane Superbases Enable the Highly Enantioselective Sulfa-Michael Addition to Fully Substituted Cyclopropene Carboxylic Acid Derivatives. Journal of the American Chemical Society, 147(44), 40045–40050.

MLA Style

Yuan, K, et al. “Bifunctional Iminophosphorane Superbases Enable the Highly Enantioselective Sulfa-Michael Addition to Fully Substituted Cyclopropene Carboxylic Acid Derivatives.” Journal of the American Chemical Society, vol. 147, no. 44, 2025, pp. 40045–50.

Chicago Style

Yuan, K, AI Ristache, SM Kosc, A Crumpton, and DJ Dixon. 2025. “Bifunctional Iminophosphorane Superbases Enable the Highly Enantioselective Sulfa-Michael Addition to Fully Substituted Cyclopropene Carboxylic Acid Derivatives.” Journal of the American Chemical Society 147 (44): 40045–50.
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Files:: Yuan_et_al_2025_Bifunctional_Iminophosphorane_Superbases.pdf

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Publisher copy:: 10.1021/jacs.5c07849

Authors

+ Yuan, K More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Chemistry Research Laboratory
Role:: Author
ORCID:: 0000-0002-6079-7299

+ Ristache, AI More by this author

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

+ Kosc, SM More by this author

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

+ Crumpton, A More by this author

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

+ Dixon, DJ More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Chemistry Research Laboratory
Role:: Author
ORCID:: 0000-0003-2456-5236

Publisher:: American Chemical Society
Journal:: Journal of the American Chemical Society More from this journal
Volume:: 147
Issue:: 44
Pages:: 40045-40050
Publication date:: 2025-10-22
Acceptance date:: 2025-09-18
DOI:: 10.1021/jacs.5c07849
EISSN:: 1520-5126
ISSN:: 0002-7863

Language:: English
Pubs id:: 2302198
UUID:: uuid_443d8228-763d-4003-a753-29acc76a42ae
Local pid:: pubs:2302198
Source identifiers:: 3446262
Deposit date:: 2025-11-06
ARK identifier:: ark:/29072/ora_443d8228763d4003a75329acc76a42ae

Terms of use

Copyright date:: 2025

Licence:: CC Attribution (CC BY)

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