Abstract
α-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 α-amino-3-piperidinylphosphonates gave, in a four-step sequence from piperidinone, the enantiopure α-amino-3-piperidinylphosphonic acids. The absolute configuration has been established by X-ray crystal structure analysis of the N -(4-nitro-benzoyl)aminophosphonate derivative.
Key words
amino acids - heterocycles - piperidines - asymmetric synthesis - addition reaction
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