Journal article

Bifunctional iminophosphorane superbases: Potent organocatalysts for enantio- and diastereoselective Michael addition reactions

Abstract:: Bifunctional iminophosphorane (BIMP) organocatalysts catalyze the enantio- and diastereoselective Michael additions of high pKacyclic malonamate ester pro-nucleophiles to nitroalkenes with reactivity profiles of up to 3 orders of magnitude greater than tertiary amine bifunctional Brønsted base/(thio)urea organocatalysts. The unrivalled performance of the BIMPs allows reaction times of challenging reactions to be slashed from weeks to minutes and has enabled new flow chemistry applications using polystyrene-supported versions contained within a flow reactor.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Farley, A., Jakubec, P., Goldys, A., & Dixon, D. (2018). Bifunctional iminophosphorane superbases: Potent organocatalysts for enantio- and diastereoselective Michael addition reactions. Tetrahedron, 74(38), 5206–5212.

MLA Style

Farley, A, et al. “Bifunctional Iminophosphorane Superbases: Potent Organocatalysts for Enantio- and Diastereoselective Michael Addition Reactions.” Tetrahedron, vol. 74, no. 38, 2018, pp. 5206–12.

Chicago Style

Farley, A, P Jakubec, A Goldys, and D Dixon. 2018. “Bifunctional Iminophosphorane Superbases: Potent Organocatalysts for Enantio- and Diastereoselective Michael Addition Reactions.” Tetrahedron 74 (38): 5206–12.
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Publisher copy:: 10.1016/j.tet.2018.06.021

Authors

+ Farley, A More by this author

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

+ Jakubec, P More by this author

Role:: Author

+ Goldys, A More by this author

Role:: Author

+ Dixon, D More by this author

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

+ Engineering & Physical Sciences Research Council More from this funder

Grant:: EP/M50659X/1

+ AstraZeneca More from this funder

+ Magdalen College, University of Oxford More from this funder

Publisher:: Elsevier
Journal:: Tetrahedron More from this journal
Volume:: 74
Issue:: 38
Pages:: 5206-5212
Publication date:: 2018-06-12
Acceptance date:: 2018-06-08
DOI:: 10.1016/j.tet.2018.06.021
EISSN:: 1464-5416
ISSN:: 0040-4020

Keywords:: Nakadomarin A

BIMP

superbase

asymmetric organocatalysis

nitroolefin

continuous flow

Michael addition
Pubs id:: pubs:870204
UUID:: uuid:6a0d470a-085a-43a9-aa2b-61effefe8086
Local pid:: pubs:870204
Source identifiers:: 870204
Deposit date:: 2018-09-11
ARK identifier:: ark:/29072/ora_6a0d470a085a43a9aa2b61effefe8086

Terms of use

Copyright date:: 2018

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

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