Asymmetric synthesis of (R)- and (S)-alpha-amino-3-piperidinylphosphonic acids via phosphite addition to iminium ions

alpha-Amino-3-piperidinylphosphonates were conveniently prepared from 3-piperidinone, by nucleophilic addition of phosphite to the iminium ion formed by in situ condensation of this ketone with chiral benzylic amines. Subsequent deprotection of N-Boc group, cleavage of the benzyl groups and acidic h...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 2; pp. 289 - 293
Main Authors Louaisil, Nicolas, Rabasso, Nicolas, Fadel, Antoine
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.01.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
asymmetric synthesis
heterocycles
ONE-POT SYNTHESIS
amino acids
piperidines
ORGANIC PHOSPHORUS-COMPOUNDS
addition reaction
AMINOPHOSPHONATES
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Summary:alpha-Amino-3-piperidinylphosphonates were conveniently prepared from 3-piperidinone, by nucleophilic addition of phosphite to the iminium ion formed by in situ condensation of this ketone with chiral benzylic amines. Subsequent deprotection of N-Boc group, cleavage of the benzyl groups and acidic hydrolysis of the resulting alpha-amino-3-piperidinylphosphonates gave, in a four-step sequence from piperidinone, the enantiopure alpha-amino-3-piperidinylphosphonic acids. The absolute configuration has been established by X-ray crystal structure analysis of the N-(4-nitrobenzoyl)aminophosphonate derivative.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-958952