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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 191, 2016 - Issue 11-12: 21st International Conference on Phosphorus Chemistry (ICPC-2016)
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Original Articles

Peptides holding a phosphonic acid: Easily recyclable organocatalysts for enantioselective C–C bond creation

Margery Cortes-ClergetUniversité Paris 13, Sorbonne Paris Cité, Laboratoire CSPBAT, CNRS UMR 7244, Bobigny, FranceCorrespondence[email protected]
,
Olivier GagerUniversité Paris 13, Sorbonne Paris Cité, Laboratoire CSPBAT, CNRS UMR 7244, Bobigny, France
,
Maëlle MonteilUniversité Paris 13, Sorbonne Paris Cité, Laboratoire CSPBAT, CNRS UMR 7244, Bobigny, France
,
Evelyne Migianu-GriffoniUniversité Paris 13, Sorbonne Paris Cité, Laboratoire CSPBAT, CNRS UMR 7244, Bobigny, France
,
Julia DeschampUniversité Paris 13, Sorbonne Paris Cité, Laboratoire CSPBAT, CNRS UMR 7244, Bobigny, France
&
Marc LecouveyUniversité Paris 13, Sorbonne Paris Cité, Laboratoire CSPBAT, CNRS UMR 7244, Bobigny, France
Pages 1593-1594 | Received 20 Jul 2016, Accepted 20 Jul 2016, Published online: 11 Aug 2016
 
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GRAPHICAL ABSTRACT

ABSTRACT

A novel bifunctional organocatalysts library was developed as efficient tool for the stereoselective Michael addition of aldehydes with several aromatic nitroalkenes. Therefore, a phosphonic acid was used for the very first time as activating moiety in the field of organocatalysis. H-R-Pro-S-Pro-R-pAla-OMe (pAla stands for phosphonoalanine) was identified as the most effective one with up to 95:5 d.r. and 93:7 e.r over 12 GABA precursors examples. This catalyst was easily recycled and reused over 10 cycles without any significant loss of selectivity.

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