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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 usi...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1016/j.tet.2018.06.021

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Wadham College
Role:
Author
Publisher:
Elsevier Publisher's website
Journal:
Tetrahedron Journal website
Volume:
74
Issue:
38
Pages:
5206-5212
Publication date:
2018-06-12
Acceptance date:
2018-06-08
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
Keywords:
Pubs id:
pubs:870204
UUID:
uuid:6a0d470a-085a-43a9-aa2b-61effefe8086
Local pid:
pubs:870204
Source identifiers:
870204
Deposit date:
2018-09-11

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