334887-07-9

Upstream product

• 762-04-9 phosphonic acid diethyl ester 
• 334887-19-3 (E)-But-2-enoic acid benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amide 
• 14231-57-3 (R)-N-benzyl-2-phenylglycinol 

Downstream Products

• 367525-88-0 {(R)-3-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-1-methyl-propyl}-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Diastereoselective synthesis of α-substituted β-amidophosphonates

A simple and general asymmetric synthesis of β-amidophosphonates is described. The method involves the highly selective addition (up to 95% d.e.) of diethyl phosphite to various chiral α,β-unsaturated carboxylic amides derived from chiral aminoalcohols.

Diastereoselective synthesis of chiral amidophosphonates by 1,5-asymmetric induction

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.