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Novel Easily Recyclable Bifunctional Phosphonic Acid Carrying Tripeptides for the Stereoselective Michael Addition of Aldehydes with Nitroalkenes
Author(s) -
CortesClerget Margery,
Gager Olivier,
Monteil Maelle,
Pirat JeanLuc,
MigianuGriffoni Evelyne,
Deschamp Julia,
Lecouvey Marc
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500794
Subject(s) - bifunctional , chemistry , stereoselectivity , michael reaction , tripeptide , catalysis , organic chemistry , selectivity , organocatalysis , solubility , combinatorial chemistry , enantioselective synthesis , amino acid , biochemistry
A novel bifunctional organocatalyst library combining both aminocatalysis and phosphonic acid activation was used for the first time as an efficient tool for the stereoselective Michael addition of aldehydes with several aromatic nitroalkenes with good selectivities up to 95:5 dr and 93:7 er . Due to their high water solubility, the catalysts were easily recyclable and could be reused over several cycles without any significant loss of selectivity.