Journal article

Bifunctional iminophosphorane-catalyzed enantioselective sulfa-michael addition to unactivated α,β-unsaturated amides

Abstract:: The first metal-free catalytic intermolecular enantioselective Michael addition to unactivated α,β-unsaturated amides is described. Consistently high enantiomeric excesses and yields were obtained over a wide range of alkyl thiol pronucleophiles and electrophiles under mild reaction conditions, enabled by a novel squaramide-based bifunctional iminophosphorane catalyst. Low catalyst loadings (2.0 mol %) were achieved on a decagram scale, demonstrating the scalability of the reaction. Computational analysis revealed the origin of the high enantiofacial selectivity via analysis of relevant transition structures and provided substantial support for specific noncovalent activation of the carbonyl group of the α,β-unsaturated amide by the catalyst.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Rozsar, D., Formica, M., Yamazaki, K., Hamlin, T. A., & Dixon, D. J. (2022). Bifunctional iminophosphorane-catalyzed enantioselective sulfa-michael addition to unactivated α,β-unsaturated amides. Journal of the American Chemical Society, 144(2), 1006–1015.

MLA Style

Rozsar, D., et al. “Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides.” Journal of the American Chemical Society, vol. 144, no. 2, American Chemical Society, 2022, pp. 1006–15.

Chicago Style

Rozsar, D, M Formica, K Yamazaki, TA Hamlin, and DJ Dixon. 2022. “Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides.” Journal of the American Chemical Society 144 (2): 1006–15.
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Files:: Rozsar_et_al_2022_Bifunctional_iminophosphorane-catalyzed.pdf

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Publisher copy:: 10.1021/jacs.1c11898

Authors

+ Rozsar, D More by this author

Role:: Author
ORCID:: 0000-0002-0516-1722

+ Formica, M More by this author

Role:: Author
ORCID:: 0000-0003-3641-7281

+ Yamazaki, K More by this author

Role:: Author
ORCID:: 0000-0002-2039-4321

+ Hamlin, TA More by this author

Role:: Author
ORCID:: 0000-0002-5128-1004

+ Dixon, DJ More by this author

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

+ Engineering & Physical Sciences Research Council More from this funder

Grant:: EP/J013501/1

+ Honjo International Scholarship Foundation More from this funder

Publisher:: American Chemical Society
Journal:: Journal of the American Chemical Society More from this journal
Volume:: 144
Issue:: 2
Pages:: 1006-1015
Publication date:: 2022-01-06
Acceptance date:: 2021-12-10
DOI:: 10.1021/jacs.1c11898
EISSN:: 1520-5126
ISSN:: 0002-7863
Pmid:: 34990142

Language:: English
Keywords:: FFR
Pubs id:: 1236432
Local pid:: pubs:1236432
Deposit date:: 2022-03-16

Terms of use

Copyright holder:: American Chemical Society
Copyright date:: 2022
Rights statement:: ©2022 American Chemical Society. This article is licensed under a Creative Commons Non-Commercial No-Derivatives License.

Licence:: CC Attribution-NonCommercial-NoDerivatives (CC BY-NC-ND)

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