Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 9, Pages 1454-1462Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob42425a
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- IKERBASQUE
- Basque Foundation for Science
- Basque Government [SAIOTEK S-PE12UN044]
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Inorganic as well as organic base catalysis was found to be effective for diastereoselective Mannich additions of malonic acid derivatives to (S-S)-N-(tert-butanesulfinyl)-3,3,3-trifluoroacetaldimine. In the presence of catalytic amounts of inorganic bases, n-BuLi or DMAP, the reaction gives the corresponding (R,S-S)-beta-aminomalonates in good yield and with diastereoselectivity up to 9/1 dr. In contrast, phosphazene bases favour the formation of the (S,S-S)-diastereomer with selectivities as high as 99/1. Simple choosing of an appropriate base catalyst for the Mannich addition reaction allowed us to obtain enantiomerically pure (R)- or (S)-configured 3-amino-4,4,4-trifluorobutanoic acids after hydrolysis and decarboxylation of the corresponding beta-aminomalonates.
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