Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 60, Pages 13829-13832Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201903572
Keywords
amino phosphonic acids; asymmetric catalysis; enantioselectivity; imino phosphonates; organocatalysis
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Funding
- JSPS KAKENHI [JP18K14869, JP18K06579]
- Tokushima University [1802001]
- Shionogi Co., Ltd.
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A practical method for synthesizing chiral alpha-amino phosphonic acid derivatives was developed. Readily available and stable N-o-nitrophenylsulfenyl (Nps) imino phosphonate was utilized as a substrate for a highly enantioselective Friedel-Crafts-type addition of indole or pyrrole nucleophiles catalyzed by chiral phosphoric acid. The resulting adduct was easily converted into N-9-fluorenylmethyloxycarbonyl (Fmoc) amino phosphonic acid, which is useful for synthesizing peptides containing an amino phosphonic acid.
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