- Diastereoselective synthesis of chiral amidophosphonates by 1,5-asymmetric induction
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We have investigated two simple diastereoselective syntheses of substituted β-amidophosphonates. The first one involved a Michael addition to α,β-unsaturated amides 6 and 8a-d, derived from chiral amino alcohols, and permitted the preparation of alkyl-substituted derivatives 7 and 9a-d with high diastereoselectivities (up to 95%) with the aid of a 1,5-asymmetric induction. The second one, involving 1,5-inductive alkylation of chiral β-amidophosphonates 14a-c, was promising in terms of the yields, but the diastereoselectivities were disappointing (up to 50%). Finally, removal of the chiral auxiliary afforded phosphonocarboxylic acid, able to provide access to a wide range of compounds of great interest for the synthesis of biologically active products.
- Castelot-Deliencourt, Geraldine,Roger, Elisabeth,Pannecoucke, Xavier,Quirion, Jean-Charles
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p. 3031 - 3038
(2007/10/03)
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