Asymmetric synthesis of functionalized tetrasubstituted α-aminophosphonates through enantioselective aza-Henry reaction of phosphorylated ketimines

Javier Vicario; Pablo Ortiz; José M. Ezpeleta; Francisco Palacios

doi:10.1021/jo502233m

Asymmetric synthesis of functionalized tetrasubstituted α-aminophosphonates through enantioselective aza-Henry reaction of phosphorylated ketimines

Javier Vicario, Pablo Ortiz, José M. Ezpeleta, Francisco Palacios^*

^*Corresponding author for this work

Bioeconomy and CO2

Research output: Contribution to journal › Article › peer-review

43 Citations (Scopus)

Abstract

Bifunctional Cinchona alkaloid thioureas efficiently catalyze asymmetric nucleophilic addition of nitromethane to ketimines derived from α-aminophosphonic acids to afford tetrasubstituted α-amino-β-nitro-phosphonates. Catalytic hydrogenation of (S)-α-amino-β-nitro-phosphonate 2d gives enantiopure (S)-α,β-diaminophosphonate 3.

Original language	English
Pages (from-to)	156-164
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	80
Issue number	1
DOIs	https://doi.org/10.1021/jo502233m
Publication status	Published - 2 Jan 2015

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abstract = "Bifunctional Cinchona alkaloid thioureas efficiently catalyze asymmetric nucleophilic addition of nitromethane to ketimines derived from α-aminophosphonic acids to afford tetrasubstituted α-amino-β-nitro-phosphonates. Catalytic hydrogenation of (S)-α-amino-β-nitro-phosphonate 2d gives enantiopure (S)-α,β-diaminophosphonate 3.",

author = "Javier Vicario and Pablo Ortiz and Ezpeleta, {Jos{\'e} M.} and Francisco Palacios",

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AU - Ezpeleta, José M.

AU - Palacios, Francisco

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AB - Bifunctional Cinchona alkaloid thioureas efficiently catalyze asymmetric nucleophilic addition of nitromethane to ketimines derived from α-aminophosphonic acids to afford tetrasubstituted α-amino-β-nitro-phosphonates. Catalytic hydrogenation of (S)-α-amino-β-nitro-phosphonate 2d gives enantiopure (S)-α,β-diaminophosphonate 3.

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Asymmetric synthesis of functionalized tetrasubstituted α-aminophosphonates through enantioselective aza-Henry reaction of phosphorylated ketimines

Abstract

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